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[ CAS No. 3695-73-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 3695-73-6
Chemical Structure| 3695-73-6
Structure of 3695-73-6 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 3695-73-6 ]

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Product Details of [ 3695-73-6 ]

CAS No. :3695-73-6 MDL No. :MFCD00065112
Formula : C5H10N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :VPZXBVLAVMBEQI-VKHMYHEASA-N
M.W : 146.14 Pubchem ID :1551643
Synonyms :
H-Gly-Ala-OH;Gly-Ala

Calculated chemistry of [ 3695-73-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.6
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 33.63
TPSA : 92.42 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.31
Log Po/w (XLOGP3) : -3.65
Log Po/w (WLOGP) : -1.47
Log Po/w (MLOGP) : -1.37
Log Po/w (SILICOS-IT) : -1.36
Consensus Log Po/w : -1.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.82
Solubility : 9600.0 mg/ml ; 65.7 mol/l
Class : Highly soluble
Log S (Ali) : 2.3
Solubility : 28900.0 mg/ml ; 198.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.29
Solubility : 282.0 mg/ml ; 1.93 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 3695-73-6 ]

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

Application In Synthesis of [ 3695-73-6 ]

* 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 [ 3695-73-6 ]

[ 3695-73-6 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 3079-63-8 ]
  • [ 3695-73-6 ]
YieldReaction ConditionsOperation in experiment
95.2% With hydrogen In methanol; water
With methanol; palladium Hydrogenolyse;
  • 2
  • [ 3695-73-6 ]
  • [ 691-80-5 ]
YieldReaction ConditionsOperation in experiment
With nitrosylchloride In formic acid
  • 3
  • [ 1871-76-7 ]
  • [ 3695-73-6 ]
  • [ 65707-75-7 ]
YieldReaction ConditionsOperation in experiment
59% With potassium hydroxide In water; benzene for 3.5h; Ambient temperature;
  • 4
  • [ 90-59-5 ]
  • [ 3695-73-6 ]
  • 2-(2-[1-(3,5-Dibromo-2-hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-acetylamino)-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium sulfate In dimethyl sulfoxide at 70℃; for 1.5h; assay condition;
  • 5
  • [ 3695-73-6 ]
  • [ 4666-16-4 ]
  • [ 153121-60-9 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane; water
  • 6
  • [ 3695-73-6 ]
  • [ 124455-85-2 ]
  • [ 132402-92-7 ]
YieldReaction ConditionsOperation in experiment
94.7% With sodium hydroxide at -25℃; α-chymotrypsin; in ice;
  • 7
  • [ 3695-73-6 ]
  • [ 68350-20-9 ]
  • [ 117803-89-1 ]
YieldReaction ConditionsOperation in experiment
37% With triethylamine In tetrahydrofuran; water for 1h; Ambient temperature;
  • 8
  • [ 4066-24-4 ]
  • [ 3695-73-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In ethanol; water
  • 9
  • [ 3695-73-6 ]
  • [ 4526-77-6 ]
YieldReaction ConditionsOperation in experiment
96% at 210 - 220℃;
96% With Zr6-based UiO-66 metal-organic frameworks at 80℃; for 24h;
95% With 14C2H7N*14H(1+)*2H2O*2O(2-)*2Zr(4+)*O122P4W34(18-) In dimethyl sulfoxide at 70℃; for 24h;
  • 10
  • [ 3695-73-6 ]
  • [ 25474-85-5 ]
  • [ 52885-35-5 ]
YieldReaction ConditionsOperation in experiment
With magnesium oxide In 1,4-dioxane
  • 11
  • [ 3695-73-6 ]
  • (5S,6S)-5-Benzoylamino-2-ethylsulfanyl-4-oxo-3,6-diphenyl-5,6-dihydro-4H-[1,3]thiazin-3-ium; sulfate [ No CAS ]
  • (S)-2-{2-[(5R,6R)-5-Benzoylamino-4-oxo-3,6-diphenyl-[1,3]thiazinan-(2E)-ylideneamino]-acetylamino}-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In ethanol for 4h; Heating;
  • 12
  • [ 3695-73-6 ]
  • (5S,6S)-5-Benzoylamino-2-ethylsulfanyl-3-(4-methoxy-phenyl)-4-oxo-6-phenyl-5,6-dihydro-4H-[1,3]thiazin-3-ium; sulfate [ No CAS ]
  • (S)-2-{2-[(5R,6R)-5-Benzoylamino-3-(4-methoxy-phenyl)-4-oxo-6-phenyl-[1,3]thiazinan-(2E)-ylideneamino]-acetylamino}-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In ethanol for 4h; Heating;
  • 13
  • [ 3695-73-6 ]
  • (5R,6R)-5-Benzoylamino-6-(4-chloro-phenyl)-2-ethylsulfanyl-4-oxo-3-phenyl-5,6-dihydro-4H-[1,3]thiazin-3-ium; sulfate [ No CAS ]
  • (S)-2-{2-[(5R,6R)-5-Benzoylamino-6-(4-chloro-phenyl)-4-oxo-3-phenyl-[1,3]thiazinan-(2E)-ylideneamino]-acetylamino}-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In ethanol for 4h; Heating;
  • 14
  • [ 3695-73-6 ]
  • (5S,6S)-5-Benzoylamino-6-(4-chloro-phenyl)-2-ethylsulfanyl-3-(4-methoxy-phenyl)-4-oxo-5,6-dihydro-4H-[1,3]thiazin-3-ium; sulfate [ No CAS ]
  • (S)-2-{2-[(5R,6R)-5-Benzoylamino-6-(4-chloro-phenyl)-3-(4-methoxy-phenyl)-4-oxo-[1,3]thiazinan-(2E)-ylideneamino]-acetylamino}-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In ethanol for 4h; Heating;
YieldReaction ConditionsOperation in experiment
With hydrogenchloride Hydrolysis;
  • 17
  • [ 3695-73-6 ]
  • [ 201296-89-1 ]
  • [ 212776-81-3 ]
YieldReaction ConditionsOperation in experiment
70% With sodium hydrogencarbonate In tetrahydrofuran at 0 - 3℃; for 1h;
  • 18
  • [ 41445-61-8 ]
  • [ 3695-73-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C15H19NO6; (S)-Ala ester salt With 4-methyl-morpholine In dichloromethane at -15 - 20℃; Stage #2: With hydrogen In methanol for 24h; Further stages.;
  • 19
  • [ 3695-73-6 ]
  • (S)-(-)-2-methylpiperazine dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 96 percent / 210 - 220 °C / 0.07 Torr 2: 19 percent / 1.) 70percent sodium bis(2-methoxyethoxy)aluminium dihydride, 2.) 4N HCl / benzene / 48 h / Heating
  • 20
  • [ 3695-73-6 ]
  • [ 153121-61-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NaHCO3, NaOH / dioxane; H2O 2: 87.4 percent / H2 / Pd/C / methanol; H2O
  • 21
  • [ 3695-73-6 ]
  • Z-Arg(Z2)-Glu(OtBu)-Gly-Ala-OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / NaHCO3, NaOH / dioxane; H2O 2: 87.4 percent / H2 / Pd/C / methanol; H2O 3: 77.6 percent / NaOH, NaHCO3 / dioxane; H2O
  • 22
  • [ 3695-73-6 ]
  • [ 117803-92-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 37 percent / N(C2H5)3 / H2O; tetrahydrofuran / 1 h / Ambient temperature 2: 43 percent / 1.) thiourea / 1.) EtOH (95percent), 60-65 deg C, 1 h; 2.) reflux, 40 min
  • 23
  • (Boc)2 O [ No CAS ]
  • [ 3695-73-6 ]
  • [ 42291-52-1 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide In tetrahydrofuran 33.B B. B. Synthesis of Boc-Gly-Ala To a solution of Gly-Ala (25.0 g, 171 mmol) in THF (350 ml) and 0.5N sodium hydroxide (350 ml) at 0° C. was added (Boc)2 O (41.3 g, 189 mmol). The pH was maintained at ~10 over a 5 h period (with 1.0N sodium hydroxide) and the reaction was stirred for 12 h thereafter at room temperature. The pH was again adjusted to ~10 with 1.0N sodium hydroxide, the THF layer was separated, and the aqueous solution was washed with ethyl acetate (2*250 ml). The pH was adjusted to 3.0 with 1.0N sodium bisulfate and this solution was extracted with ethyl acetate (2*250 ml). The combined extracts were dried (magnesium sulfate), filtered and concentrated in vacuo to afford 38.2 g (91% yield) of the product as a white powder: 1 H NMR (DMSO-d6) δ 1.26 (d, J=7.3 Hz, 3 H), 1.38 (s, 9 H), 3.45-3.62 (m, 2 H), 4.18-4.25 (m, 1 H), 6.88 (t, J=5.6 Hz, 1 H), 7.99 (d, J=7.2 Hz, 1 H).
  • 24
  • (BOC)20 [ No CAS ]
  • [ 3695-73-6 ]
  • [ 42291-52-1 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide In tetrahydrofuran 33.B B. B. Synthesis of Boc-Gly-Ala To a solution of Gly-Ala (25.0 g, 171 mmol) in THF (350 ml) and 0.5N sodium hydroxide (350 ml) at 0° C. was added (Boc)20 (41.3 g, 189 mmol). The pH was maintained at ~10 over a 5 h period (with 1.0N sodium hydroxide) and the reaction was stirred for 12 h thereafter at room temperature. The pH was again adjusted to ~10 with 1.0N sodium hydroxide, the THF layer was separated, and the aqueous solution was washed with ethyl acetate (2*250 ml). The pH was adjusted to 3.0 with 1.0N sodium bisulfate and this solution was extracted with ethyl acetate (2*250 ml). The combined extracts-were dried (magnesium sulfate), filtered and concentrated in vacuo to afford 38.2 g (91% yield) of the product as a white powder: 1 H NMR (DMSO-d6) δ 1.26 (d, J=7.3 Hz, 3 H), 1.38 (s, 9 H), 3.45-3.62 (m, 2 H), 4.18-4.25 (m, 1 H), 6.88 (t, J=5.6 Hz, 1 H), 7.99 (d, J=7.2 Hz, 1 H).
  • 25
  • [ 3695-73-6 ]
  • nickel(II) perchlorate [ No CAS ]
  • [ 32270-34-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In water Electrolysis; slow addn. of NaOH to a soln. of Ni(ClO4)2 containing fivefold excess of S-glycylalanine to pH 11, filtration, oxidized by electrolysis (700 mV, flow cell); purified on QAE-Sephadex resin (eluent: 0.10 M NaClO4), not isolated;
  • 26
  • Co(imidazolate)2 [ No CAS ]
  • [ 3695-73-6 ]
  • Co(N(CH)2NHCH)(NH2CH2CONCH(CH3)COO)(H2O)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water In water byproducts: NH(CH)2NCH, Co(CH3CH(NH2)CONCH2COO)2; under O2-free atmosphere, dissolution of Co(imid)2 in the isoelectric dipeptide medium; addn. of acetone, pptn. of complex and unreacted dipeptide; not isolated, detected by UV;
  • 27
  • copper(II) perchlorate hexahydrate [ No CAS ]
  • [ 3695-73-6 ]
  • glycyl-L-alaninato copper(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol In water educts mixed, pH raised to 6.78 by addition of NaOH, concd. to a small vol. under vac., adding ethanol; soln. cooled in a refrigerator for several hs, product pptd.; elem. anal;
  • 28
  • (CO)3Mn((C5H3)(CH(CH3)N(CH3)2)(CHNCH2CONCuCH(CH3)COO)) [ No CAS ]
  • [ 3695-73-6 ]
  • (+)-(R(c),R(f))-2(α-(N,N-dimethylamino)ethyl)formylcymantrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium carbonate In water acid hydrolysis by addn. of 3N HCl, then neutralized by Na2CO3, extd. with CCl4;
  • 29
  • (CO)3Mn((C5H3)(CH(CH3)N(CH3)2)(CHNCH2CONCuCH(CH3)COO)) [ No CAS ]
  • [ 3695-73-6 ]
  • (+)-(R(c),S(f))-2(α-(N,N-dimethylamino)ethyl)formylcymantrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium carbonate In water acid hydrolysis by addn. of 3N HCl, then neutralized by Na2CO3, extd. with CCl4;
  • 30
  • cobalt(II) chloride hexahydrate [ No CAS ]
  • [ 3695-73-6 ]
  • K(1+)*[Co(NH2CH2C(O)NCH(CH3)COO)2](1-)*2.5H2O=K[Co(NH2CH2C(O)NCH(CH3)COO)2]*2.5H2O [ No CAS ]
  • K(1+)*[Co(NH2CH2C(O)NCH(CH3)COO)2](1-)*H2O=K[Co(NH2CH2C(O)NCH(CH3)COO)2]*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; potassium chloride; lead dioxide In water dissolving of peptide in water, aq. NaOH addn. to pH 9-9.5, aq. CoCl2 dropwise addn. (keeping pH at 9 with aq. NaOH), stirring with PbO2 at 40°C for 1 h, filtration, chromy. (QAE-Sephadex A-25/Cl(1-), H2O then 0.05M KCl); concn. at 35-40°C, CH3OH addn., filtration, concn., chromy. (Sephadex G-10), concn., crystn. by CH3OH or acetone addn. to aq. soln., cooling, filtration, washing, vac. drying over CaCl2, UV and CD anal.;
  • 31
  • [ 3695-73-6 ]
  • 2H(1+)*PtCl6(2-)*5H2O=H2(PtCl6)*5H2O [ No CAS ]
  • [ 7681-11-0 ]
  • K(Pt(glyα-ala)Cl3)*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With KOH; AgNO3 In water byproducts: AgI, AgCl, KNO3; aq. soln. KI was added to aq. soln. H2(PtCl6)*5H2O and heated to 70° for 2 min, aq. soln. H2dipep was added and heated for 2 h, pH was adjusted to 5.5-6.5 with 1 M KOH every 5 min, aq. soln. AgNO3 was addd andstirred for 10 min; AgI and AgCl were filtered off, soln. was concd. and added to water/methanol 1:4, KNO3 was filtered off, filtrate was evapd. to dryness; elem. anal.;
  • 32
  • [ 3695-73-6 ]
  • [ 58-63-9 ]
  • copper dichloride [ No CAS ]
  • Cu(NH2CH2CONHCHCH3COOH)(C5H6O(OH)3C5H3N4O)2(2+)*2Cl(1-)*9H2O=[Cu(NH2CH2CONHCHCH3COOH)(C5H6O(OH)3C5H3N4O)2]Cl2*9H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With H2O In ethanol; water heating and stirring (70°C); cooling to 25°C, filtn., adding EtOH, filtn., washing (EtOH, H2O,EtOH, Et2O); elem. anal.;
  • 33
  • [ 3695-73-6 ]
  • [ 118-00-3 ]
  • copper dichloride [ No CAS ]
  • Cu(NH2CH2CONHCHCH3COOH)(C5H6O(OH)3C5H4N5O)2(2+)*2Cl(1-)*7H2O=[Cu(NH2CH2CONHCHCH3COOH)(C5H6O(OH)3C5H4N5O)2]Cl2*7H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With H2O In ethanol; water heating and stirring (70°C); cooling to 25°C, filtn., adding EtOH, filtn., washing (EtOH, H2O,EtOH, Et2O); elem. anal.;
  • 34
  • gold(III) tetrachloride trihydrate [ No CAS ]
  • [ 3695-73-6 ]
  • AuCl(NH2CH2CONCHCH3COO) [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With ammonium hydroxide In water soln. of HAuCl4*3H2O in H2O added to aq. soln. of ligand, pH adjusted to4.0 by NH4OH, 2 wk; ppt. filtered, washed with water, dried over P2O5; elem. anal.;
  • 35
  • [ 112-16-3 ]
  • [ 3695-73-6 ]
  • [ 910792-03-9 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In water Cooling with ice;
  • 36
  • [ 3695-73-6 ]
  • [ 79-03-8 ]
  • [ 1089175-99-4 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydroxide In water Cooling with ice;
  • 37
  • [ 3695-73-6 ]
  • [ 98-88-4 ]
  • [ 24639-11-0 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide In water Cooling with ice;
  • 38
  • [ 3695-73-6 ]
  • [ 122-04-3 ]
  • [ 1089176-01-1 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide In water Cooling with ice;
  • 39
  • [ 3695-73-6 ]
  • [ 142-61-0 ]
  • [ 1089176-00-0 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide In water Cooling with ice;
  • 40
  • [ 3695-73-6 ]
  • [ 112-67-4 ]
  • [ 1334169-74-2 ]
YieldReaction ConditionsOperation in experiment
In sodium hydroxide Synthesis of (2S)-2-[[2-(hexadecanoylamino)acetyl]amino]propanoic acid Synthesis of (2S)-2-[[2-(hexadecanoylamino)acetyl]amino]propanoic acid (2S)-2-[[2-(hexadecanoylamino)acetyl]amino]propanoic acid is obtained by preparing a first solution by dissolving Glycyl-L-alanine (30 mmol) in Sodium hydroxide (0.105 M, 300 mL). This first solution is placed in a round bottomed flask with an efficient magnetic stirrer. The flask is completely immersed in an ice bath and during the reaction and the magnetic stirrer is set at 1800 rpm. Palmitoyl chloride (12.37 grams, 45 mmol) and sodium hydroxide (3M, 15 mL) are drop wise added to this first solution at the same rate in such a way that the pH of the reaction mixture does not decrease below 10. When the reaction is completed, the suspension is acidified carefully with chloride acid 2M. The residue obtained after filtration (filtering plate n° 3) is extracted with petroleum ether to remove the fatty acid. The resulting white solid is dried under vacuum oven (PSelecta) at 60° C. for 24 h. The yield obtained is 94%. (2S)-2-[[2-(hexadecanoylamino)acetyl]amino]propanoic acid is characterize using infrared, 1H NMR and 13C NMR obtaining following results: IR (KBr): 3379, 3290, 2916, 2849, 1728, 1651, 1625, 1537 cm-1. 1H NMR (300 MHz, [D6]DMSO, 30° C.): δ 12.33 (s, 1H), 8.03 (d, J=6.8 Hz, 1H), 7.93 (m, 1H), 4.26-4.11 (m, 1H), 3.77-3.59 (m, 2H), 2.13 (dt, J=20.2, 7.0 Hz, 2H), 1.46 (m, 5H), 1.22 (m, 24H), 0.84 (m, 3H) ppm. 13CNMR (75 MHz, [D6]DMSO, 30° C.): δ=174.63, 173.16, 169.40, 48.10, 42.31, 35.87, 31.99, 29.76, 29.55, 29.41, 25.87, 22.78, 17.99, 14.56 ppm.
  • 41
  • [ 3695-73-6 ]
  • [ 1342794-15-3 ]
  • [ 1342794-38-0 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine In water; acetonitrile at 0℃;
  • 42
  • [ 3695-73-6 ]
  • [ 1342794-05-1 ]
  • [ 1342794-11-9 ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine In water; acetonitrile at 0℃;
  • 43
  • [ 850232-61-0 ]
  • [ 3695-73-6 ]
  • [ 1385775-68-7 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In water; acetonitrile at 20℃;
  • 44
  • [ 3695-73-6 ]
  • [ 1385775-69-8 ]
  • [ 1385775-75-6 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: glycyl-L-alanine; N-(N'-Cbz-L-Phe-L-Cys)-1H-benzotriazole With triethylamine In water; acetonitrile at 0 - 20℃; for 2h; Stage #2: With hydrogenchloride In water; acetonitrile
  • 45
  • [ 3695-73-6 ]
  • [ 56-41-7 ]
  • [ 56-40-6 ]
YieldReaction ConditionsOperation in experiment
With sodium orthovanadate * 2 water; water In water-d2 at 60℃;
With 15K(1+)*H(1+)*25H2O*O122P4W34Zr(16-); water; hydrogen chloride In water-d2 at 60℃;
With K15H[Zr(α2-P2W17O61)2]*25H2O; water-d2 at 60℃;
With hydrogenchloride; potassium chloride In water at 70℃; General Procedure for Measuring the Kinetics of the Hydrolysis of Peptides by NMRSpectroscopy General procedure: A 10 mL solution with 50 mm peptide, 1.0 m HCl, and 4 m NaCl or KCl wasprepared in a 20 mL scintillation vial. The reaction mixture was stirred at 70 C for the duration of the experiment. At various time intervals, a 250 L aliquot of the sample was removed fromthe reaction and diluted with 250 L of D2O in an NMR tube for analysis.
With hydrogenchloride; sodium chloride In water at 70℃; General Procedure for Measuring the Kinetics of the Hydrolysis of Peptides by NMRSpectroscopy General procedure: A 10 mL solution with 50 mm peptide, 1.0 m HCl, and 4 m NaCl or KCl wasprepared in a 20 mL scintillation vial. The reaction mixture was stirred at 70 C for the duration of the experiment. At various time intervals, a 250 L aliquot of the sample was removed fromthe reaction and diluted with 250 L of D2O in an NMR tube for analysis.

  • 46
  • tetrabutylphosphonium alaninate [ No CAS ]
  • [ 5680-79-5 ]
  • [ 3695-73-6 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: tetrabutylphosphonium alaninate; glycine ethyl ester hydrochloride at 60℃; for 24h; Inert atmosphere; Stage #2: With acetic acid In chloroform at 20℃; for 3h;
  • 47
  • Fmoc-alanine-Wang-resin [ No CAS ]
  • [ 29022-11-5 ]
  • [ 3695-73-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-alanine-Wang-resin With piperidine In N,N-dimethyl-formamide for 0.166667h; Stage #2: N-(fluoren-9-ylmethoxycarbonyl)glycine With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 1h; Further stages; 11 Gly-Pro-Ala-Gly-Pro (SEQ ID NO: 2) shown in Table 1 was synthesized by an Fmoc solid phase 18 synthesis method using an automatic peptide synthesizer (433A) manufactured by Applied Biosystems. The synthesis was carried out by a stepwise elongation method comprising supporting an amino acid corresponding to the C-terminal of oligopeptide to a resin and elongating one amino acid toward the N-terminal, and diisopropylcarbodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) were used as condensing agents in a peptide coupling reaction which corresponds to an elongation reaction. Note that while the amino group of amino acid which was allowed to elongate toward the N terminal was protected by 9-fluorenylmethyloxycarbonyl (Fmoc), amino acids that compose the oligopeptide did not contain side chains with a reaction activity and thus the side chain was not in particular protected. First, 0.5 g of Fmoc-Pro-Wang resin (0.5 to 0.8 mmol/g, manufactured by Bachem) obtained by protecting the N-terminal of Pro which corresponded to the C-terminal of the oligopeptide, and supporting on a Wang resin through the C-terminal thereof was used. This was put in a reaction vessel of an automatic peptide synthesizer and deprotection of Fmoc was carried out a 20% piperidin-DMF solution for 10 minutes. The resin was washed with DMF for one minute and then Fmoc-Gly-OH, DIC, and HOBt were added 1 mmol each to the reaction solution. The reaction was carried out for one hour. Thereafter, it was made sure that unreacted N termini were not detected and then the resultant was washed with DMF for one minute. Further, deprotection of Fmoc was carried out with 20% piperidin-DMF; the resin was washed with DMF; and then Fmoc-Ala-OH, DIC, and HOBt were added thereto 1 mmol each to allow a reaction. Subsequently, the above procedure was carried out for Pro and Gly by the same method to elongate amino acids one by one. The obtained Fmoc-Gly-Pro-Ala-Gly-Pro-Wang (SEQ ID NO: 23) resin was deprotected with a 20% piperidin-DMF solution for 10 minutes and was dried under reduced pressure. The obtained dried resin was treated with TFA (10 mL×3 times) and an oligopeptide crude product was eluted from the resin into TFA. The obtained TFA solution was distilled under reduced pressure at room temperature and then diethyl ether 10 mL was added to residues while cooling on ice to obtain a precipitate. Further, the precipitate was washed with diethyl ether (10 mL×5 times) and the resulting precipitate was dried under reduced pressure. The weight of the thus obtained crude product was 38.5 mg (yield 29.8%). The obtained crude product was dissolved in purified water and fractionated to purify by reversed phase high pressure liquid chromatography (HPLC). The purity of the obtained purified product was checked by thin layer chromatography (TLC) and HPLC, and the amino acid sequence thereof was determined by Edman method. It was then confirmed by a mass spectrometer (MALDI-TOF) that the intended molecular weight was attained. The final weight of intended product was 30.7 mg and the yield thereof was 23.8%.
  • 48
  • [ 64-17-5 ]
  • [ 3695-73-6 ]
  • N,N-di-ethylglycylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) In neat (no solvent) at 90℃; for 24h; Schlenk technique; Inert atmosphere; 4 General reaction conditions General procedure: General procedure, 0.2 or 0.5 mmol 4, 2 mmol or 5 ml 2, neat or with solvent (amount shown in the table), 1 mol % Cat 2, 18 or 24 h, 90°C, isolated yields in parenthesis; "Conversion and selectivities are based on crude H NMR.
  • 49
  • [ 111-29-5 ]
  • [ 3695-73-6 ]
  • N,N-di-(5-hydroxypentyl)glycylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); 2,2,2-trifluoroethanol In toluene at 90℃; for 24h; Schlenk technique; Inert atmosphere; 4 General reaction conditions General procedure: General procedure, 0.2 or 0.5 mmol 4, 2 mmol or 5 ml 2, neat or with solvent (amount shown in the table), 1 mol % Cat 2, 18 or 24 h, 90°C, isolated yields in parenthesis; "Conversion and selectivities are based on crude H NMR.
  • 50
  • [ 3695-73-6 ]
  • [ 112-53-8 ]
  • N,N-di-(n-dodecyl)glycylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); 2,2,2-trifluoroethanol In toluene at 90℃; for 18h; Schlenk technique; Inert atmosphere; 4 General reaction conditions General procedure: General procedure, 0.2 or 0.5 mmol 4, 2 mmol or 5 ml 2, neat or with solvent (amount shown in the table), 1 mol % Cat 2, 18 or 24 h, 90°C, isolated yields in parenthesis; "Conversion and selectivities are based on crude H NMR.
  • 51
  • [ 3695-73-6 ]
  • [ 127-17-3 ]
  • pyruvoylglycylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% Stage #1: 2-oxo-propionic acid With p-toluenesulfonyl chloride In acetone for 0.333333h; Stage #2: glycyl-L-alanine With pyridine In water; acetone at 0 - 20℃; Synthesis ofpyruvoylglycine (8a) Tosylation was performed according to a literature approach(Dixon 1964) with some modifications. Tosyl chloride (2.4377g, 12.8mmol) was dissolved in 6.25mL acetone(dried over anhydrous sodium sulfate) and cooled down to0°C in an ice bath. Pyruvic acid (0.875mL, 12.6mmol)was slowly added to the solution with stirring, and thenpyridine (1.025mL, 12.7mmol) was mixed in at 0°C. Themixture was stirred for 20min and afterwards, a solutionof glycine (0.9375g, 12.5mmol) and pyridine (2.125mL,26mmol) in water (8.75mL) was added dropwise at 0°C.The mixture was allowed to warm to room temperature andrapidly stirred until the previously formed precipitate haddissolved. The solution was reduced to dryness in vacuo.The residue was dissolved in 20mL water, acidified with1mL 12M hydrochloric acid and extracted with ethyl acetate(4 × 100mL). The organic phases were combined, driedover sodium sulfate and evaporated to dryness in vacuo. Thecrude product was dissolved in 10mL water, neutralizedwith 50 μL 5M sodium hydroxide and chromatographedon a 1.5 × 50cm glass column filled with 80mL of stronglybasic anion-exchange resin (AG 1-X8, BioRad Lab, Munich,Germany), previously regenerated and preconditioned bysuccessive application of 300mL 1M sodium hydroxide,600mL water, 300mL 1M hydrochloric acid and washedneutral with 600mL water. The elution was performed with4M acetic acid (500mL). The fractions were collected inseparate 5mL tubes using a BioRad 2110 Fraction collector.Samples (50 μL) of each fraction were mixed with 50 μL of0.1% (m/v) solution of DNPH in 2M hydrochloric acid andincubated at room temperature for 5min. The mixtures werethen extracted with 250 μL ethyl acetate. The organic phaseswere separated and extracted with 350 μL 0.4M sodiumcarbonate buffer, pH 9.6. Of each aqueous solution, 100 μLwas transferred to a microtiter plate, and the absorbance at365nm was measured using the plate reader Tecan InfiniteM200 Pro (Tecan Group, Männedorf, Switzerland) The fractions51-67 (out of total 100) were tested positively (photometrically)and further characterized using HPLC-MS/MS.Fractions that contained the product were combined, dried invacuo and lyophilized. The yield was 27.9mg (0.192mmol,molar yield = 3%).
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