(3R)-3-amino-5-(methylsulfanyl)pentanoic acid

Base Information

• Chemical Name: (3R)-3-amino-5-(methylsulfanyl)pentanoic acid
• CAS No.: 75946-25-7
• Molecular Formula: C₆H₁₃NO₂S
• Molecular Weight: 163.241
• Nikkaji Number: J1.925.968D
• Mol file: 75946-25-7.mol

Synonyms:75946-25-7;(R)-3-Amino-5-(methylthio)pentanoic acid;L-beta-homomethionine;(3R)-3-amino-5-(methylsulfanyl)pentanoic acid;D-beta-homomethionine;L-Beta-homomethionine, HCl;(3R)-3-amino-5-methylsulfanylpentanoic acid;B3M;beta-L-homomethionine;SCHEMBL13254782;CHEBI:136681;MFCD28387584;AKOS027430398;DS-3437;FD10029;FD10030;(R)-3-Amino-5-(methylthio)pentanoicacid;(R)-3-[2-(Methylthio)ethyl]-beta-alanine;CS-0062044;EN300-199894;Q27458200

Chemical Property of (3R)-3-amino-5-(methylsulfanyl)pentanoic acid

Chemical Property:

• Vapor Pressure: 0.000192mmHg at 25°C
• Boiling Point: 305.1 °C at 760 mmHg
• PKA: 3.71±0.10(Predicted)
• Flash Point: 138.3 °C
• PSA: 88.62000
• Density: 1.164±0.06 g/cm3(Predicted)
• LogP: 2.04380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 163.06669983
• Heavy Atom Count: 10
• Complexity: 108

Purity/Quality:

98%Min ^*data from raw suppliers

L-beta-Homomethionine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(CC(=O)O)N
• Isomeric SMILES: CSCC[C@@H](CC(=O)O)N

Technology Process of (3R)-3-amino-5-(methylsulfanyl)pentanoic acid

There total 2 articles about (3R)-3-amino-5-(methylsulfanyl)pentanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

5-(methylthio)-3-oxopentanoic acid → (R)-β-homomethionine (75946-25-7,1217975-36-4,158570-14-0)

Guidance literature:

With 2,3,4,5,6-pentahydroxy-hexanal; nicotinamide adenine dinucleotide phosphate; freeze-dried D-glucose dehydrogenase from Bacillus subtilis; ammonium chloride; In aq. buffer; for 4h; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/anie.202017225

Reference yield:

5-methylsulfanyl-3-oxo-pentanoic acid ethyl ester (118123-92-5) → (R)-β-homomethionine (75946-25-7,1217975-36-4,158570-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: immobilized lipase; ammonium chloride / dimethyl sulfoxide / 3 h / 30 °C / pH Ca_. 8.5 / Enzymatic reaction

2: nicotinamide adenine dinucleotide phosphate; ammonium chloride; 2,3,4,5,6-pentahydroxy-hexanal; freeze-dried D-glucose dehydrogenase from Bacillus subtilis / aq. buffer / 4 h / Enzymatic reaction

With 2,3,4,5,6-pentahydroxy-hexanal; immobilized lipase; nicotinamide adenine dinucleotide phosphate; freeze-dried D-glucose dehydrogenase from Bacillus subtilis; ammonium chloride; In dimethyl sulfoxide;

DOI:10.1002/anie.202017225

Reference yield:

(R)-β-homomethionine (75946-25-7,1217975-36-4,158570-14-0) → (R)-3-(2,4-Dinitro-phenylamino)-5-methylsulfanyl-pentanoic acid (4-methoxy-phenyl)-amide (78175-28-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Sanger's procedure

2: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-hydroxybenzotriazole / CH₂Cl₂

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1016/S0040-4039(01)92514-6

upstream raw materials:

5-methylsulfanyl-3-oxo-pentanoic acid ethyl ester

Downstream raw materials:

(R)-3-(2,4-Dinitro-phenylamino)-5-methylsulfanyl-pentanoic acid

(R)-3-(2,4-Dinitro-phenylamino)-5-methylsulfanyl-pentanoic acid (4-methoxy-phenyl)-amide

Refernces