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Chemical Structure| 72040-64-3 Chemical Structure| 72040-64-3
Chemical Structure| 72040-64-3

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Synonyms: N-(+)-Biotinyl-6-aminohexanoic acid

4.5 *For Research Use Only !

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Product Details of N-Biotinyl-6-aminohexanoic acid

CAS No. :72040-64-3
Formula : C16H27N3O4S
M.W : 357.47
SMILES Code : O=C(O)CCCCCNC(CCCC[C@@H]1SC[C@]([C@]1([H])N2)([H])NC2=O)=O
Synonyms :
N-(+)-Biotinyl-6-aminohexanoic acid
MDL No. :MFCD00144853
InChI Key :CMUGHZFPFWNUQT-HUBLWGQQSA-N
Pubchem ID :446905

Safety of N-Biotinyl-6-aminohexanoic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of N-Biotinyl-6-aminohexanoic acid

* 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 [ 72040-64-3 ]

[ 72040-64-3 ] Synthesis Path-Downstream   1~54

  • 1
  • 12-aminododecanoic acid methyl ester hydrochloride [ No CAS ]
  • [ 72040-64-3 ]
  • [ 223733-85-5 ]
  • 2
  • [ 170892-94-1 ]
  • [ 72040-64-3 ]
  • Biotinylaminocaproyl-L-methionylglycyl-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester [ No CAS ]
  • 3
  • Glycyl-(S-palmitoyl)-L-cysteine allyl ester hydrotrifluoroacetate [ No CAS ]
  • [ 72040-64-3 ]
  • Biotinylaminocaproyl-glycyl-(S-palmitoyl)-L-cysteine allyl ester [ No CAS ]
  • 4
  • [ 72040-64-3 ]
  • Glycyl-(S-hexadecyl)-L-cysteine allyl ester hydrotrifluoroacetate [ No CAS ]
  • Biotinylaminocaproyl-glycyl-(S-hexadecyl)-L-cysteine allyl ester [ No CAS ]
  • 5
  • [ 72040-64-3 ]
  • poly(sebacic acid) [ No CAS ]
  • fluorescein-conjugated avidin [ No CAS ]
  • 6-((biotinoyl)amino)hexanoic acid-attached poly(sebacic acid) microspheres [ No CAS ]
  • 6
  • methyl 6-(+)-biotinylamidohexanoate [ No CAS ]
  • [ 72040-64-3 ]
YieldReaction ConditionsOperation in experiment
58.3% With lithium hydroxide monohydrate; In methanol;Reflux; Lithium hydroxide (4equiv) solution was added to 6 (1equiv) dissolved in methanol. The solution was heated to reflux overnight. The product 7 was precipitated as white solid. Then a hydrochloric acid solution (6 N) was added until the pH was 5. The product was filtered, and dried under vacuum.
  • 7
  • [ 4136-95-2 ]
  • [ 72040-64-3 ]
  • C23H28Cl3N3O5S [ No CAS ]
  • 8
  • [ 162827-97-6 ]
  • [ 72040-64-3 ]
  • [ 721431-24-9 ]
  • 9
  • [ 66534-97-2 ]
  • [ 72040-64-3 ]
  • 5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoic acid {5-[bis(2-diphenylphosphanyl-ethyl)carbamoyl]pentyl}amide [ No CAS ]
  • 10
  • [ 144085-40-5 ]
  • [ 72040-64-3 ]
  • 6-[5-(2-oxohexahydrothieno[3,4-d]imidazol-4-yl)pentanoylamino]hexanoic acid {3-diphenylphosphanyl-2-[(diphenylphosphanyl)methyl]-2-methylpropyl}amide [ No CAS ]
  • 11
  • [ 72040-64-3 ]
  • [ 774183-16-3 ]
  • methyl 2-cyano-23-[6-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}amino)hexanoyl]oxy-3,12-dioxooleana-1,9(11)-dien-28-oate [ No CAS ]
  • 12
  • [ 58-85-5 ]
  • [ 60-32-2 ]
  • [ 72040-64-3 ]
  • 13
  • [ 7689-03-4 ]
  • [ 72040-64-3 ]
  • 6-biotinylaminocaproic acid-(20s)-camptothecin [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With dmap; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 48h;Inert atmosphere; General procedure: To a mixture of Biotin or 6-biotinylaminocaproic acid (0.3 mmol), camptothecin analogues (0.1 mmol) and DMF (2.5 mL) was added, 4-Dimethylaminopyridine (DMAP) (0.01 mmol) was added and N, N'-Diisopropylcarbodiimide) (DIC) (0.6 mmol) dropwise. The reaction mixture was stirred at room temperature for 2 days under N2. Solvent were removed under a reduced. The residue was purified on a silica gel chromatography (CHCl3:CH3OH = 15:1?9:1) to afford the product Biotin-(20s)-camptothecin (11). Yellow amorphous powder, yield 60percent;
  • 14
  • glycine rapamycin ester [ No CAS ]
  • [ 72040-64-3 ]
  • C69H107N5O17S [ No CAS ]
  • 15
  • [ 56-41-7 ]
  • [ 72040-64-3 ]
  • (S)-2-{6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-propionic acid [ No CAS ]
  • 16
  • [ 61-90-5 ]
  • [ 72040-64-3 ]
  • (S)-4-Methyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-pentanoic acid [ No CAS ]
  • 17
  • [ 63-68-3 ]
  • [ 72040-64-3 ]
  • [ 217655-55-5 ]
  • 18
  • [ 56-85-9 ]
  • [ 72040-64-3 ]
  • (S)-4-Carbamoyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyric acid [ No CAS ]
  • 19
  • [ 74-79-3 ]
  • [ 72040-64-3 ]
  • (S)-5-Guanidino-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-pentanoic acid [ No CAS ]
  • 20
  • [ 63-91-2 ]
  • [ 72040-64-3 ]
  • (S)-2-{6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-3-phenyl-propionic acid [ No CAS ]
  • 21
  • [ 912557-14-3 ]
  • [ 72040-64-3 ]
  • [(S)-2-((S)-3-Methyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyrylamino)-propionylamino]-acetic acid (2E,4E)-hexa-2,4-dienyl ester [ No CAS ]
  • 22
  • [ 861640-70-2 ]
  • [ 72040-64-3 ]
  • [ 861640-71-3 ]
  • 23
  • p-aminophenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->3)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • [ 72040-64-3 ]
  • [(6-biotinylamido)hexanoylamido]-phenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->3)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 24
  • p-aminophenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->6)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • [ 72040-64-3 ]
  • [(6-biotinylamido)hexanoylamido]-phenyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl-2-onic acid-(2->6)-β-D-galactopyranoside-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 25
  • C21H22N2O2 [ No CAS ]
  • [ 72040-64-3 ]
  • C37H47N5O5S [ No CAS ]
  • 26
  • [ 72040-64-3 ]
  • (S)-4-Methylsulfanyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyric acid 4-nitro-phenyl ester [ No CAS ]
  • 27
  • [ 72040-64-3 ]
  • (S)-4-Methylsulfanyl-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester [ No CAS ]
  • 28
  • [ 72040-64-3 ]
  • [ 446878-26-8 ]
  • 29
  • [ 72040-64-3 ]
  • [ 446878-23-5 ]
  • 30
  • [ 72040-64-3 ]
  • [ 446878-21-3 ]
  • 31
  • [ 72040-64-3 ]
  • [ 446878-22-4 ]
  • 32
  • [ 72040-64-3 ]
  • [ 446878-24-6 ]
  • 33
  • [ 72040-64-3 ]
  • 14-hydroxy-3β-{6-[5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido]hexanoyloxy}-5β,14β-card-20(22)-enolide [ No CAS ]
  • 34
  • [ 72040-64-3 ]
  • 22-(4-benzoylbenzoyloxy)-14-hydroxy-3β-{6-[5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido]hexanoyloxy}-5β,14β-card-20(22)-enolide [ No CAS ]
  • 37
  • [ 72040-64-3 ]
  • [ 223733-86-6 ]
  • 38
  • [ 72040-64-3 ]
  • 1-O-(α-D-galactopyranosyl)-2-<N-12-(6-(biotinoylamino)hexanoylamino)dodecanoylamino>-octadecanol [ No CAS ]
  • 39
  • [ 72040-64-3 ]
  • (2S,3R)-1-O-(α-D-galactopyranosyl)-2-<N-12-(6-(biotinoylamino)hexanoylamino)dodecanoylamino>-1,3-octadecanediol [ No CAS ]
  • 40
  • [ 72040-64-3 ]
  • (2S,3S,4R)-1-O-(β-D-galactopyranosyl)-2-<N-12-(6-(biotinoylamino)hexanoylamino)dodecanoylamino>-1,3,4-octadecanetriol [ No CAS ]
  • 41
  • [ 72040-64-3 ]
  • (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-<N-12-(6-(biotinoylamino)hexanoylamino)dodecanoylamino>-1,3,4-octadecanetriol [ No CAS ]
  • 42
  • [ 648903-77-9 ]
  • [ 72040-64-3 ]
  • 2-{4-[6-(biotinamido)hexanamido]phenylamino}-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;N,N-dimethyl-formamide; In dichloromethane; for 12h; 2- (4-AMINOPHENYLAMINO)-6- (2, 6-DICHLOROPHENYL)-8-METHYL-8H-PYRIDO [2, 3-D] PYRIMIDIN-7- one, SKI DV1-10, (55 mg, 0.133 mmol), N- (+)-BIOTINYL-6-AMINOCAPROIC acid (57.2 mg, 0.160 mmol), 1- [3- (DIMETHYLAMINO) PROPYL]-3-ETHYLCARBODIIMIDE hydrochloride (123 mg, 0.64 mmol), and 4-dimethylaminopyridine (78 mg, 0.64 mmol) were combined in a 10 mL flame-dried round bottomed flask under argon. The solids were suspended in 5 mL of methylene chloride and a few drops of dimethylformamide. The solution was stirred for 12 hours. The reaction was poured into a separatory funnel containing 50 mL of methylene chloride. The organic layer was washed with three 50 mL portions of water and once with 50 mL of saturated brine. The organic layer was dried over magnesium sulfate, the drying agent removed by filtration and the solvent removed. The crude residue was purified by gradient silica gel column chromatography (0-15 percent 7M ammonia/ methanol in methylene chloride). The product containing fractions were combined and evaporated. The product was pure by standard analytical techniques.
  • 43
  • [ 883720-36-3 ]
  • [ 72040-64-3 ]
  • [ 883720-37-4 ]
YieldReaction ConditionsOperation in experiment
73.4% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 0.5h; Benzophenone-biotin: N-(+)-Biotinyl-6-aminohexanoic acid (239 mg) and 4~benzoyl-L-phenylalanyl-6-aminoxehanoic acid methyl ester (237 mg) were dissolved in DMF, 230 mul of DIPEA were added to the reaction mixture, followed by 237 mg of HBTU. The reaction mixture was stirred at RT for 30 min. LC-MS analysis showed complete reaction. The solvent and excess of DIPEA were removed under high vacuum. The crude product was dissolved in CHCl3 and extracted 2X with 1percent HCl. Organic phase was separated, solvent was removed and the product was purified using rotary chromatography (SiO2 solid phase). Yield 325 mg (73.4percent).
  • 44
  • [ 72040-64-3 ]
  • [ 518-28-5 ]
  • [ 1041187-72-7 ]
  • 45
  • [ 5680-79-5 ]
  • [ 72040-64-3 ]
  • C19H32N4O5S [ No CAS ]
  • 46
  • [ 1176084-23-3 ]
  • [ 1176084-10-8 ]
  • [ 72040-64-3 ]
  • C133H254N22O46S6 [ No CAS ]
  • 47
  • C30H35N2O4Pol [ No CAS ]
  • [ 72040-64-3 ]
  • C46H60N5O7PolS [ No CAS ]
  • 48
  • C37H39N2O5Pol [ No CAS ]
  • [ 72040-64-3 ]
  • C53H64N5O8PolS [ No CAS ]
  • 49
  • C30H34ClN2O4Pol [ No CAS ]
  • [ 72040-64-3 ]
  • C46H59ClN5O7PolS [ No CAS ]
  • 50
  • C31H37N2O5Pol [ No CAS ]
  • [ 72040-64-3 ]
  • C47H62N5O8PolS [ No CAS ]
  • 51
  • C32H39N2O4Pol [ No CAS ]
  • [ 72040-64-3 ]
  • C48H64N5O7PolS [ No CAS ]
  • 52
  • C31H34N3O4Pol [ No CAS ]
  • [ 72040-64-3 ]
  • C47H59N6O7PolS [ No CAS ]
  • 53
  • C30H34ClN2O5Pol [ No CAS ]
  • [ 72040-64-3 ]
  • C46H59ClN5O8PolS [ No CAS ]
  • 54
  • C33H36N3O4Pol [ No CAS ]
  • [ 72040-64-3 ]
  • C49H61N6O7PolS [ No CAS ]
 

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