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[ CAS No. 4235-95-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4235-95-4
Chemical Structure| 4235-95-4
Structure of 4235-95-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4235-95-4 ]

CAS No. :4235-95-4 MDL No. :MFCD00135191
Formula : C44H84NO8P Boiling Point : -
Linear Structure Formula :C36H68NPO8(CH2)8 InChI Key :SNKAWJBJQDLSFF-NVKMUCNASA-N
M.W : 786.11 Pubchem ID :10350317
Synonyms :
DOPC;sn-3-Dioleoyllecithin;PC(18:1(9Z)/18:1(9Z));18:1 (Δ9-Cis) PC;PDD 111;1,2-DOPC;1,2-Dioleoyl-sn-glycero-3-PC
Chemical Name :(R)-2,3-Bis(oleoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate

Calculated chemistry of [ 4235-95-4 ]

Physicochemical Properties

Num. heavy atoms : 54
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 42
Num. H-bond acceptors : 8.0
Num. H-bond donors : 0.0
Molar Refractivity : 228.08
TPSA : 121.0 Ų

Pharmacokinetics

GI absorption : None
BBB permeant : None
P-gp substrate : None
CYP1A2 inhibitor : None
CYP2C19 inhibitor : None
CYP2C9 inhibitor : None
CYP2D6 inhibitor : None
CYP3A4 inhibitor : None
Log Kp (skin permeation) : None cm/s

Lipophilicity

Log Po/w (iLOGP) : None
Log Po/w (XLOGP3) : None
Log Po/w (WLOGP) : 12.79
Log Po/w (MLOGP) : None
Log Po/w (SILICOS-IT) : None
Consensus Log Po/w : None

Druglikeness

Lipinski : None
Ghose : None
Veber : None
Egan : None
Muegge : None
Bioavailability Score : None

Water Solubility

Log S (ESOL) : None
Solubility : None mg/ml ; None mol/l
Class : None
Log S (Ali) : None
Solubility : None mg/ml ; None mol/l
Class : None
Log S (SILICOS-IT) : None
Solubility : None mg/ml ; None mol/l
Class : None

Medicinal Chemistry

PAINS : None alert
Brenk : None alert
Leadlikeness : None
Synthetic accessibility : None

Safety of [ 4235-95-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4235-95-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4235-95-4 ]

[ 4235-95-4 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 112-77-6 ]
  • [ 28319-77-9 ]
  • [ 4235-95-4 ]
  • 2
  • [ 6085-36-5 ]
  • [ 28319-77-9 ]
  • [ 4235-95-4 ]
  • 3
  • [ 28319-77-9 ]
  • [ 18175-45-6 ]
  • [ 4235-95-4 ]
  • 4
  • [ 2788-84-3 ]
  • [ 4235-95-4 ]
  • (Z)-Octadec-9-enoic acid (R)-2-[((S)-2-amino-2-methoxycarbonyl-ethoxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 5
  • [ 672-15-1 ]
  • [ 4235-95-4 ]
  • [ 62-49-7 ]
  • [ 108824-18-6 ]
  • 6
  • [ 4048-33-3 ]
  • [ 4235-95-4 ]
  • (Z)-Octadec-9-enoic acid (R)-2-[(6-amino-hexyloxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 7
  • [ 14742-23-5 ]
  • [ 4235-95-4 ]
  • 1,2-dioleoyl-sn-glycero-3-phosphatidylethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; calcium chloride In diethyl ether for 15h; Ambient temperature; peanut phospholipase D;
  • 8
  • [ 55357-38-5 ]
  • C39H71Cl2O6P [ No CAS ]
  • [ 4235-95-4 ]
YieldReaction ConditionsOperation in experiment
With pyridine In chloroform for 14h; Ambient temperature; Yield given;
  • 9
  • [ 4235-95-4 ]
  • [ 132295-44-4 ]
  • (Z)-Octadec-9-enoic acid (S)-2-[((2S,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-pyrrolidin-2-ylmethoxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 10
  • [ 4235-95-4 ]
  • [ 100937-52-8 ]
  • (Z)-Octadec-9-enoic acid (R)-2-[((2R,3R,4R)-3,4-dihydroxy-pyrrolidin-2-ylmethoxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 11
  • [ 4235-95-4 ]
  • SerGly(OMe) [ No CAS ]
  • (Z)-Octadec-9-enoic acid (R)-2-[(S)-2-amino-2-(methoxycarbonylmethyl-carbamoyl)-ethoxy]-hydroxy-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 12
  • [ 4235-95-4 ]
  • Ser-Gly-Val-OMe [ No CAS ]
  • (Z)-Octadec-9-enoic acid (R)-2-[((S)-2-amino-2-[((S)-1-methoxycarbonyl-2-methyl-propylcarbamoyl)-methyl]-carbamoyl}-ethoxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 13
  • [ 4235-95-4 ]
  • (S)-2-[(S)-3-Carboxy-2-(2-{(S)-5-guanidino-2-[2-(6-hydroxy-hexanoylamino)-acetylamino]-pentanoylamino}-acetylamino)-propionylamino]-3-methyl-butyric acid methyl ester [ No CAS ]
  • C65H117N8O17P [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 14
  • [ 4235-95-4 ]
  • [ 534-03-2 ]
  • (Z)-Octadec-9-enoic acid (R)-2-[(2-amino-3-hydroxy-propoxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 15
  • [ 4235-95-4 ]
  • [ 56-81-5 ]
  • 1,2-dioleoyl-sn-glycero-3-[phospho-rac-(1-glycerol)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 16
  • [ 4235-95-4 ]
  • [ 147-94-4 ]
  • (Z)-Octadec-9-enoic acid (R)-2-[(2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With CaCl2 buffer; sodium acetate; acetic acid In chloroform at 30℃; for 4h; phospholipase D from Streptomyces sp., pH 6.5;
  • 17
  • [ 4235-95-4 ]
  • [ 135598-68-4 ]
  • C49H82N4O11P(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% In chloroform; water at 40℃; phospholipase D from Streptomyces sp. AA 586;
  • 18
  • C6H13NO*H(1+) [ No CAS ]
  • [ 4235-95-4 ]
  • (Z)-Octadec-9-enoic acid (R)-2-[hydroxy-(1-methyl-piperidin-4-yloxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With acetate buffer; calcium chloride In diethyl ether; water at 25℃; for 20h; phospholipase D from Streptomyces sp. (PLD Type VII);
  • 19
  • [ 32465-43-3 ]
  • [ 4235-95-4 ]
  • C46H86NO8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With acetate buffer; calcium chloride In diethyl ether; water at 25℃; for 20h; phospholipase D from Streptomyces sp. (PLD Type VII);
  • 20
  • [ 39895-81-3 ]
  • [ 4235-95-4 ]
  • C44H84AsO8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With acetate buffer; calcium chloride In diethyl ether; water at 25℃; for 7h; phospholipase D from Streptomyces sp. (PLD Type VII);
  • 21
  • [ 4235-95-4 ]
  • [ 45733-02-6 ]
  • C47H88NO8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With acetate buffer; calcium chloride In diethyl ether; water at 25℃; for 7h; phospholipase D from Streptomyces sp. (PLD Type VII);
  • 22
  • [ 4235-95-4 ]
  • C7H15NO*H(1+) [ No CAS ]
  • (Z)-Octadec-9-enoic acid (R)-2-[hydroxy-(2-piperidin-1-yl-ethoxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With acetate buffer; calcium chloride In diethyl ether; water at 25℃; for 4h; phospholipase D from Streptomyces sp. (PLD Type VII);
  • 23
  • [ 4235-95-4 ]
  • 4-Hydroxy-1,1-dimethyl-azepanium [ No CAS ]
  • C47H88NO8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With acetate buffer; calcium chloride In diethyl ether; water at 25℃; for 2.7h; phospholipase D from cabbage;
  • 26
  • [ 425-75-2 ]
  • [ 4235-95-4 ]
  • 1,2-dioleoyl-sn-glycero-3-ethylphosphocholine triflate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform at 20℃;
  • 27
  • 2-(1',2'-dioleoyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane [ No CAS ]
  • [ 75-50-3 ]
  • [ 4235-95-4 ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine In acetonitrile at 20℃; for 16h;
  • 28
  • [ 75-50-3 ]
  • [ 4235-95-4 ]
YieldReaction ConditionsOperation in experiment
With benzene
YieldReaction ConditionsOperation in experiment
With cadmium(II) chloride Behandeln des Addukts mit Oleylchlorid und Pyridin in Chloroform;
  • 30
  • [ 4235-95-4 ]
  • 1,2-dioleoyl-sn-glycero-3-phosphocholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With azobis(dimethylvaleronitrile); 2-hydroxyethanethiol In <i>tert</i>-butyl alcohol at 54℃; for 4h;
  • 31
  • [ 4235-95-4 ]
  • trifluoro-methanesulfonic acid 4-(1,3-dioxo-1<i>H</i>,3<i>H</i>-benzo[<i>de</i>]isoquinolin-2-yl)-butyl ester [ No CAS ]
  • (2-{(2,3-bis-octadec-9-enoyloxy-propoxy)-[4-(1,3-dioxo-1<i>H</i>,3<i>H</i>-benzo[<i>de</i>]isoquinolin-2-yl)-butoxy]-phosphoryloxy}-ethyl)-trimethyl-ammonium; trifluoro-methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; chloroform at 20℃;
  • 32
  • [ 112-80-1 ]
  • [ 28319-77-9 ]
  • [ 4235-95-4 ]
  • 33
  • [ 4235-95-4 ]
  • [ 50-89-5 ]
  • C41H69N2PO12(CH2)8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.7% With D-glucose In chloroform; acetate buffer at 37℃; for 1h;
  • 34
  • [ 4235-95-4 ]
  • polymer; monomer(s): 1,2-dioleoyl-sn-glycero-3-phosphocholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In water at 60℃; sonication;
  • 35
  • [ 24529-88-2 ]
  • [ 4235-95-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / Et3N / benzene / 16 h / 20 °C 2: 64 percent / Et3N / acetonitrile / 16 h / 20 °C
Multi-step reaction with 2 steps 1: POCl3, Et3N / CHCl3 / 0.5 h / 0 °C 2: pyridine / CHCl3 / 14 h / Ambient temperature
  • 36
  • [ 22202-46-6 ]
  • [ 4235-95-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 73 percent / 12N HCl / CHCl3; methanol / 18 h / 0 °C 2: 93 percent / Et3N / benzene / 16 h / 20 °C 3: 64 percent / Et3N / acetonitrile / 16 h / 20 °C
  • 37
  • oleic anhydride [ No CAS ]
  • [ 4235-95-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 66 percent 2: 80 percent
  • 38
  • [ 4235-95-4 ]
  • (Z)-Octadec-9-enoic acid (R)-2-[((S)-3,6-dioxo-piperazin-2-ylmethoxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 mM NaOAc, 50 mM CaCl2 buffer, AcOH / CHCl3 / 4 h / 30 °C / phospholipase D from Streptomyces sp., pH 6.5 2: SiO2, NH3*H2O / CHCl3; methanol
  • 39
  • [ 143997-01-7 ]
  • [ 4235-95-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichlorodicyanobenzoquinone (DDQ) / CH2Cl2; H2O / 4 h / 20 °C 2: POCl3, Et3N / CHCl3 / 0.5 h / 0 °C 3: pyridine / CHCl3 / 14 h / Ambient temperature
  • 40
  • [ 102-71-6 ]
  • [ 4235-95-4 ]
  • 1,2-dioleoyl-sn-glycerophospho-triethanolamine [ No CAS ]
  • bis(1,2-dioleoyl-sn-glycerophospho)triethanolamine [ No CAS ]
  • [ 61617-08-1 ]
YieldReaction ConditionsOperation in experiment
22.6% With phospholipase D from cabbage In diethyl ether; acetate buffer at 30℃; for 8h;
  • 41
  • [ 6976-37-0 ]
  • [ 4235-95-4 ]
  • C47H90NO12P [ No CAS ]
  • [ 61617-08-1 ]
YieldReaction ConditionsOperation in experiment
19.6% With phospholipase D from Streptomyces sp. (Type VII) In diethyl ether; acetate buffer at 30℃; for 5h;
  • 42
  • [ 4235-95-4 ]
  • [ 534-03-2 ]
  • 1,2-dioleoyl-sn-glycerophospho-serinol [ No CAS ]
  • bis(1,2-dioleoyl-sn-glycerophospho)serinol [ No CAS ]
  • [ 61617-08-1 ]
YieldReaction ConditionsOperation in experiment
39.5% With phospholipase D from cabbage In diethyl ether; acetate buffer at 30℃; for 8h;
  • 43
  • [ 106-24-1 ]
  • [ 4235-95-4 ]
  • phosphatidylgeraniol [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium acetate buffer; albumin In ethyl acetate at 37℃; for 24h;
  • 44
  • [ 106-28-5 ]
  • [ 4235-95-4 ]
  • phosphatidylfarnesol [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium acetate buffer; albumin In ethyl acetate at 37℃; for 24h;
  • 45
  • [ 253686-88-3 ]
  • [ 4235-95-4 ]
  • phosphatidylphytol [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With sodium acetate buffer; albumin In ethyl acetate at 37℃; for 24h;
  • 46
  • [ 24034-73-9 ]
  • [ 4235-95-4 ]
  • phosphatidylgeranylgeraniol [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With sodium acetate buffer; albumin In ethyl acetate at 37℃; for 24h;
  • 47
  • [ 4235-95-4 ]
  • [ 112-80-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: dioleoylphosphatidylcholine With 4-morpholineethanesulfonic acid; Phospholipase A<SUB>1</SUB>-1 from Armillaria ostoyae; sodium hydroxide at 30℃; Enzymatic reaction; Stage #2: With N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid
  • 48
  • [ 61413-67-0 ]
  • [ 4235-95-4 ]
  • [ 1421945-04-1 ]
YieldReaction ConditionsOperation in experiment
28% In chloroform Inert atmosphere; Reflux;
  • 49
  • [ 66542-51-6 ]
  • [ 4235-95-4 ]
  • [ 1421945-06-3 ]
YieldReaction ConditionsOperation in experiment
28% In chloroform Inert atmosphere; Reflux;
  • 50
  • [ 4235-95-4 ]
  • α-chloroethyl n-hexanoate [ No CAS ]
  • [ 1421945-07-4 ]
YieldReaction ConditionsOperation in experiment
21% In chloroform Inert atmosphere; Reflux;
  • 51
  • [ 5402-53-9 ]
  • [ 4235-95-4 ]
  • [ 1421945-08-5 ]
YieldReaction ConditionsOperation in experiment
29% In chloroform Inert atmosphere; Reflux;
  • 52
  • [ 1421486-25-0 ]
  • [ 4235-95-4 ]
  • [ 1421945-09-6 ]
YieldReaction ConditionsOperation in experiment
31% In chloroform Inert atmosphere; Reflux;
  • 53
  • [ 192571-02-1 ]
  • [ 4235-95-4 ]
  • [ 1421945-10-9 ]
YieldReaction ConditionsOperation in experiment
55% In chloroform Inert atmosphere; Reflux;
  • 54
  • [ 1421487-20-8 ]
  • [ 4235-95-4 ]
  • [ 1421945-11-0 ]
YieldReaction ConditionsOperation in experiment
27% In chloroform Inert atmosphere; Reflux;
  • 55
  • [ 1421486-26-1 ]
  • [ 4235-95-4 ]
  • [ 1421945-12-1 ]
YieldReaction ConditionsOperation in experiment
26% In chloroform Inert atmosphere; Reflux;
  • 56
  • [ 4235-95-4 ]
  • [ 65657-60-5 ]
  • [ 1421945-05-2 ]
YieldReaction ConditionsOperation in experiment
38% In chloroform Inert atmosphere; Reflux;
  • 57
  • [ 4235-95-4 ]
  • [ 61-73-4 ]
  • C44H84NO8P*C34H24N6O14S4(4-)*4Na(1+) [ No CAS ]
  • 58
  • [ 57-09-0 ]
  • [ 4235-95-4 ]
  • [ 61-73-4 ]
  • 2C19H42N(1+)*2Br(1-)*C34H24N6O14S4(4-)*4Na(1+)*2C44H84NO8P [ No CAS ]
  • 59
  • [ 57-09-0 ]
  • [ 4235-95-4 ]
  • [ 61-73-4 ]
  • C19H42N(1+)*Br(1-)*C44H84NO8P*C34H24N6O14S4(4-)*4Na(1+) [ No CAS ]
  • 60
  • [ 57-09-0 ]
  • [ 4235-95-4 ]
  • [ 61-73-4 ]
  • 3C19H42N(1+)*3Br(1-)*3C44H84NO8P*C34H24N6O14S4(4-)*4Na(1+) [ No CAS ]
  • 61
  • [ 573-58-0 ]
  • [ 4235-95-4 ]
  • C32H22N6O6S2(2-)*2Na(1+)*C44H84NO8P [ No CAS ]
  • 62
  • [ 57-09-0 ]
  • [ 573-58-0 ]
  • [ 4235-95-4 ]
  • C32H22N6O6S2(2-)*2Na(1+)*C19H42N(1+)*Br(1-)*C44H84NO8P [ No CAS ]
  • 63
  • [ 57-09-0 ]
  • [ 573-58-0 ]
  • [ 4235-95-4 ]
  • C32H22N6O6S2(2-)*2Na(1+)*2C19H42N(1+)*2Br(1-)*2C44H84NO8P [ No CAS ]
  • 64
  • [ 57-09-0 ]
  • [ 573-58-0 ]
  • [ 4235-95-4 ]
  • C32H22N6O6S2(2-)*2Na(1+)*3C19H42N(1+)*3Br(1-)*3C44H84NO8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tafazzin from Saccharomyces cerevisiae In aq. buffer at 37℃; Enzymatic reaction; Measurement of Transacylation Activity of Tafazzin in Liposomes General procedure: Isolated tafazzin (4.0 g) was incubated with PC/MLCL, PC/DLCL, or LPC/DLCL liposomes in 85 μl of reaction buffer (50 mM Tris-HCl, pH 7.4) at 37 °C, and the final lipid concentration was 0.59 mM. The final concentrations of Triton X-100, which were introduced into a reaction mixture with the enzyme, were maximally 0.08%. We confirmed by dynamic light scattering measurements that the particle size distribution of liposomes is maintained under the assay conditions, as shown in Fig. 9B taking PC(18:1-18:1)/sn-2-MLCL(18:1-18:1/18:1-OH) liposomes (9:1 molar ratio) as an example. The reaction was quenched after definite incubation periods by the addition of 5 μl of solvent A (CH3CN/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume) and 5 μl of solvent B (2-propanol/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume). Note that the enzyme reaction was quenched within 20s by this treatment. To accurately quantify lipid products, we directly subjected the reaction samples, without an extraction step using an organic solvent, to the HPLC analysis described below. The recovery of products in our HPLC analytical method was greater than 95%.
YieldReaction ConditionsOperation in experiment
With tafazzin from Saccharomyces cerevisiae In aq. buffer at 37℃; Enzymatic reaction; Measurement of Transacylation Activity of Tafazzin in Liposomes General procedure: Isolated tafazzin (4.0 g) was incubated with PC/MLCL, PC/DLCL, or LPC/DLCL liposomes in 85 μl of reaction buffer (50 mM Tris-HCl, pH 7.4) at 37 °C, and the final lipid concentration was 0.59 mM. The final concentrations of Triton X-100, which were introduced into a reaction mixture with the enzyme, were maximally 0.08%. We confirmed by dynamic light scattering measurements that the particle size distribution of liposomes is maintained under the assay conditions, as shown in Fig. 9B taking PC(18:1-18:1)/sn-2-MLCL(18:1-18:1/18:1-OH) liposomes (9:1 molar ratio) as an example. The reaction was quenched after definite incubation periods by the addition of 5 μl of solvent A (CH3CN/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume) and 5 μl of solvent B (2-propanol/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume). Note that the enzyme reaction was quenched within 20s by this treatment. To accurately quantify lipid products, we directly subjected the reaction samples, without an extraction step using an organic solvent, to the HPLC analysis described below. The recovery of products in our HPLC analytical method was greater than 95%.
YieldReaction ConditionsOperation in experiment
With tafazzin from Saccharomyces cerevisiae In aq. buffer at 37℃; Enzymatic reaction; Measurement of Transacylation Activity of Tafazzin in Liposomes General procedure: Isolated tafazzin (4.0 g) was incubated with PC/MLCL, PC/DLCL, or LPC/DLCL liposomes in 85 μl of reaction buffer (50 mM Tris-HCl, pH 7.4) at 37 °C, and the final lipid concentration was 0.59 mM. The final concentrations of Triton X-100, which were introduced into a reaction mixture with the enzyme, were maximally 0.08%. We confirmed by dynamic light scattering measurements that the particle size distribution of liposomes is maintained under the assay conditions, as shown in Fig. 9B taking PC(18:1-18:1)/sn-2-MLCL(18:1-18:1/18:1-OH) liposomes (9:1 molar ratio) as an example. The reaction was quenched after definite incubation periods by the addition of 5 μl of solvent A (CH3CN/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume) and 5 μl of solvent B (2-propanol/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume). Note that the enzyme reaction was quenched within 20s by this treatment. To accurately quantify lipid products, we directly subjected the reaction samples, without an extraction step using an organic solvent, to the HPLC analysis described below. The recovery of products in our HPLC analytical method was greater than 95%.
  • 68
  • C45H84O15P2(2-)*2H4N(1+) [ No CAS ]
  • [ 4235-95-4 ]
  • C81H148O17P2(2-)*2H4N(1+) [ No CAS ]
  • [ 19420-56-5 ]
YieldReaction ConditionsOperation in experiment
With tafazzin from Saccharomyces cerevisiae; In aq. buffer; at 37℃;pH 7.4;Enzymatic reaction;Kinetics; General procedure: Isolated tafazzin (4.0 g) was incubated with PC/MLCL, PC/DLCL, or LPC/DLCL liposomes in 85 mul of reaction buffer (50 mM Tris-HCl, pH 7.4) at 37 C, and the final lipid concentration was 0.59 mM. The final concentrations of Triton X-100, which were introduced into a reaction mixture with the enzyme, were maximally 0.08%. We confirmed by dynamic light scattering measurements that the particle size distribution of liposomes is maintained under the assay conditions, as shown in Fig. 9B taking PC(18:1-18:1)/sn-2-MLCL(18:1-18:1/18:1-OH) liposomes (9:1 molar ratio) as an example. The reaction was quenched after definite incubation periods by the addition of 5 mul of solvent A (CH3CN/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume) and 5 mul of solvent B (2-propanol/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume). Note that the enzyme reaction was quenched within 20s by this treatment. To accurately quantify lipid products, we directly subjected the reaction samples, without an extraction step using an organic solvent, to the HPLC analysis described below. The recovery of products in our HPLC analytical method was greater than 95%.
  • 69
  • C63H116O16P2(2-)*2H4N(1+) [ No CAS ]
  • [ 4235-95-4 ]
  • C81H148O17P2(2-)*2H4N(1+) [ No CAS ]
  • [ 19420-56-5 ]
YieldReaction ConditionsOperation in experiment
With tafazzin from Saccharomyces cerevisiae; In aq. buffer; at 37℃;pH 7.4;Enzymatic reaction;Kinetics; General procedure: Isolated tafazzin (4.0 g) was incubated with PC/MLCL, PC/DLCL, or LPC/DLCL liposomes in 85 mul of reaction buffer (50 mM Tris-HCl, pH 7.4) at 37 C, and the final lipid concentration was 0.59 mM. The final concentrations of Triton X-100, which were introduced into a reaction mixture with the enzyme, were maximally 0.08%. We confirmed by dynamic light scattering measurements that the particle size distribution of liposomes is maintained under the assay conditions, as shown in Fig. 9B taking PC(18:1-18:1)/sn-2-MLCL(18:1-18:1/18:1-OH) liposomes (9:1 molar ratio) as an example. The reaction was quenched after definite incubation periods by the addition of 5 mul of solvent A (CH3CN/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume) and 5 mul of solvent B (2-propanol/H2O/(C2H5)3N/CH3COOH, 89:10:0.5:0.5 by volume). Note that the enzyme reaction was quenched within 20s by this treatment. To accurately quantify lipid products, we directly subjected the reaction samples, without an extraction step using an organic solvent, to the HPLC analysis described below. The recovery of products in our HPLC analytical method was greater than 95%.
  • 70
  • [ 51166-72-4 ]
  • [ 4235-95-4 ]
  • 3C48H84O30*C44H84NO8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water-d2 at 20℃; for 6h;
  • 71
  • [ 51166-71-3 ]
  • [ 4235-95-4 ]
  • 3C56H98O35*C44H84NO8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; water-d2 at 25℃;
  • 72
  • C126H132N6O9 [ No CAS ]
  • [ 4235-95-4 ]
  • C126H132N6O9*C44H84NO8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform-d1 at 24.84℃;
  • 73
  • [ 1421487-04-8 ]
  • [ 4235-95-4 ]
  • C67H129NO15P(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
290 mg In chloroform for 20h; Inert atmosphere; Reflux;
  • 74
  • [ 1421487-05-9 ]
  • [ 4235-95-4 ]
  • C69H133NO15P(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
174 mg In chloroform for 20h; Inert atmosphere; Reflux;
  • 75
  • [ 1421487-06-0 ]
  • [ 4235-95-4 ]
  • C69H131NO16P(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
147 mg In chloroform for 20h; Inert atmosphere; Reflux;
  • 76
  • [ 5274-68-0 ]
  • [ 358-23-6 ]
  • [ 4235-95-4 ]
  • C64H125NO12P(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: tetraethylene glycol monododecyl ether; trifluoromethylsulfonic anhydride With pyridine Stage #2: dioleoylphosphatidylcholine
  • 77
  • [ 1421487-03-7 ]
  • [ 4235-95-4 ]
  • C66H127NO15P(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
130 mg In chloroform for 20h; Inert atmosphere; Reflux;
  • 78
  • [ 23214-92-8 ]
  • [ 4235-95-4 ]
  • C66H100NO18P [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With calcium chloride; phospholipase D In hexane at 45℃; Darkness; Enzymatic reaction;
  • 79
  • [ 4235-95-4 ]
  • [ 19420-56-5 ]
  • [ 22248-65-3 ]
  • 80
  • [ 4235-95-4 ]
  • [ 525-66-6 ]
  • O-oleoyl propranolol [ No CAS ]
  • N-oleoyl propranolol [ No CAS ]
  • [ 19420-56-5 ]
  • [ 22248-65-3 ]
  • 81
  • [ 4235-95-4 ]
  • [ 107-19-7 ]
  • C42H75O8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
With PLD enzimes (A. hypogaea) Enzymatic reaction; Use of Alkynyl Alcohols for Imaging in Fixed Cells Only General procedure: The first experiments assessed whether PLD would accept alkynols as substrates in vitro. A panel of five small alkynols (propynol, 3-butyn-1-ol, 4-pentyn-1-ol, 5-hexyn-1-ol, and 6-heptyn-1-ol) were evaluated by incubating each with 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and a commercially available PLD. The reaction mixtures were then subjected to CuAAC with an azide-labeled rhodamine 110 derivative (Az488). HPLC separation coupled to fluorescence or electrospray ionization-mass spectrometry (ESI-MS) detection confirmed the identity of the expected fluorescent phosphatidyl alcohol products for all five alkynols. A general schematic of the process is provided in FIG. 2A.
  • 82
  • [ 4235-95-4 ]
  • [ 638-45-9 ]
  • 1,2-dioleoyl-sn-glycero-3-hexylphosphocholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% In tetrahydrofuran at 50℃; Inert atmosphere; Synthesis of Alkylated DOPC General procedure: 1,2-Dioleoyl-sn-glycero-3-hexylphosphocholine, 1,2-dioleoyl-sn-glycero-3-heptylphosphocholine,and 1,2-dioleoyl-sn-glycero-3-octylphosphocholine(hexyl-, heptyl-, and octyl-DOPC, respectively) were synthesizedby a method modified from that previously reported28,30):DOPC (0.79 g, 1.0 mmol) in CHCl3 was added to flasks andthe solvent was evaporated and dried in vacuum. Tetrahydrofuran (4.0 mL) and 1-iodohexane, 1-iodoheptane, or1-iodooctane (2.0 mmol) were added to these flasks, and thereaction mixture was stirred overnight at 50°C under argon.The solvent was evaporated and the crude product was purifiedusing silica gel flash chromatography eluting with agradient of 0-10% MeOH/CHCl3 to afford pure product (50%yield): 1H-NMR (CDCl3, 400 MHz) δ (ppm): 5.34-5.27 (q,4H), 5.26-5.20 (m, 1H), 4.58-4.00 (m, 10H), 3.56-3.49 (s,9H), 2.34-2.27 (m, 4H), 2.01-1.94 (m, 8H), 1.69-1.62 (q, 2H),1.60-1.54 (m, 4H), 1.30-1.20 (m, 38-42H), 0.90-0.81 (m,9H); TLC Rf 0.67 (CHCl3 : MeOH : H2O; 60 : 30 : 4); the exactmass calculated for [C50H97NO8P]+ requires m/z 870.6952,observed 870.6955 (positive fast ion bombardment, FAB+),[C51H99NO8P]+ requires m/z 884.7108, observed 884.7108(FAB+), [C52H101NO8P]+ requires m/z 898.7265, observed898.7252 (FAB+).
  • 83
  • [ 4282-40-0 ]
  • [ 4235-95-4 ]
  • 1,2-dioleoyl-sn-glycero-3-heptylphosphocholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% In tetrahydrofuran at 50℃; Inert atmosphere; Synthesis of Alkylated DOPC General procedure: 1,2-Dioleoyl-sn-glycero-3-hexylphosphocholine, 1,2-dioleoyl-sn-glycero-3-heptylphosphocholine,and 1,2-dioleoyl-sn-glycero-3-octylphosphocholine(hexyl-, heptyl-, and octyl-DOPC, respectively) were synthesizedby a method modified from that previously reported28,30):DOPC (0.79 g, 1.0 mmol) in CHCl3 was added to flasks andthe solvent was evaporated and dried in vacuum. Tetrahydrofuran (4.0 mL) and 1-iodohexane, 1-iodoheptane, or1-iodooctane (2.0 mmol) were added to these flasks, and thereaction mixture was stirred overnight at 50°C under argon.The solvent was evaporated and the crude product was purifiedusing silica gel flash chromatography eluting with agradient of 0-10% MeOH/CHCl3 to afford pure product (50%yield): 1H-NMR (CDCl3, 400 MHz) δ (ppm): 5.34-5.27 (q,4H), 5.26-5.20 (m, 1H), 4.58-4.00 (m, 10H), 3.56-3.49 (s,9H), 2.34-2.27 (m, 4H), 2.01-1.94 (m, 8H), 1.69-1.62 (q, 2H),1.60-1.54 (m, 4H), 1.30-1.20 (m, 38-42H), 0.90-0.81 (m,9H); TLC Rf 0.67 (CHCl3 : MeOH : H2O; 60 : 30 : 4); the exactmass calculated for [C50H97NO8P]+ requires m/z 870.6952,observed 870.6955 (positive fast ion bombardment, FAB+),[C51H99NO8P]+ requires m/z 884.7108, observed 884.7108(FAB+), [C52H101NO8P]+ requires m/z 898.7265, observed898.7252 (FAB+).
  • 84
  • [ 629-27-6 ]
  • [ 4235-95-4 ]
  • 1,2-dioleoyl-sn-glycero-3-octylphosphocholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% In tetrahydrofuran at 50℃; Inert atmosphere; Synthesis of Alkylated DOPC General procedure: 1,2-Dioleoyl-sn-glycero-3-hexylphosphocholine, 1,2-dioleoyl-sn-glycero-3-heptylphosphocholine,and 1,2-dioleoyl-sn-glycero-3-octylphosphocholine(hexyl-, heptyl-, and octyl-DOPC, respectively) were synthesizedby a method modified from that previously reported28,30):DOPC (0.79 g, 1.0 mmol) in CHCl3 was added to flasks andthe solvent was evaporated and dried in vacuum. Tetrahydrofuran (4.0 mL) and 1-iodohexane, 1-iodoheptane, or1-iodooctane (2.0 mmol) were added to these flasks, and thereaction mixture was stirred overnight at 50°C under argon.The solvent was evaporated and the crude product was purifiedusing silica gel flash chromatography eluting with agradient of 0-10% MeOH/CHCl3 to afford pure product (50%yield): 1H-NMR (CDCl3, 400 MHz) δ (ppm): 5.34-5.27 (q,4H), 5.26-5.20 (m, 1H), 4.58-4.00 (m, 10H), 3.56-3.49 (s,9H), 2.34-2.27 (m, 4H), 2.01-1.94 (m, 8H), 1.69-1.62 (q, 2H),1.60-1.54 (m, 4H), 1.30-1.20 (m, 38-42H), 0.90-0.81 (m,9H); TLC Rf 0.67 (CHCl3 : MeOH : H2O; 60 : 30 : 4); the exactmass calculated for [C50H97NO8P]+ requires m/z 870.6952,observed 870.6955 (positive fast ion bombardment, FAB+),[C51H99NO8P]+ requires m/z 884.7108, observed 884.7108(FAB+), [C52H101NO8P]+ requires m/z 898.7265, observed898.7252 (FAB+).
Same Skeleton Products
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