s-Glycerylcysteine

Base Information

• Chemical Name: s-Glycerylcysteine
• CAS No.: 23255-32-5
• Molecular Formula: C6H13 N O4 S
• Molecular Weight: 195.24
• Hs Code.: 2930909090
• Mol file: 23255-32-5.mol

Synonyms:s-glycerylcysteine;SCHEMBL788419;GPWYBXDQHZIBPR-AKGZTFGVSA-N;AKOS017531670;S-(2,3-dihydroxy) propyl-l-cysteine

Chemical Property of s-Glycerylcysteine

Chemical Property:

• Vapor Pressure: 6.74E-11mmHg at 25°C
• Boiling Point: 472.1°Cat760mmHg
• Flash Point: 239.3°C
• PSA: 128.59000
• Density: 1.386g/cm³
• LogP: -1.29690
• XLogP3: -4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 195.05652907
• Heavy Atom Count: 12
• Complexity: 144

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of s-Glycerylcysteine

There total 4 articles about s-Glycerylcysteine 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: 67.0%

1-bromo-2,3-propanediol (4704-77-2) + l-cysteine hydrochloride (52-89-1) → S-<(2RS)-2,3-Dihydroxypropyl>-L-Cys-OH (23255-32-5)

Guidance literature:

With triethylamine; In water; for 72h; Darkness;

DOI:10.1039/c5sc03859f

Reference yield: 17.0%

S-<(2RS)-2,3-Dihydroxypropyl>-Nα-Boc-Cys-OBut (134982-22-2,134982-23-3,134982-24-4,134982-25-5) → S-<(2RS)-2,3-Dihydroxypropyl>-L-Cys-OH (23255-32-5)

Guidance literature:

With methyl-phenyl-thioether; trifluoroacetic acid; for 1h; Ambient temperature;

DOI:10.1248/cpb.39.607

Reference yield:

2-amino-3-chloropropanoic acid (2731-73-9) + rac-3-sulfanylpropane-1,2-diol (96-27-5) → S-<(2RS)-2,3-Dihydroxypropyl>-L-Cys-OH (23255-32-5)

Guidance literature:

With potassium phosphate; In water; at 37 ℃; for 24h; enzyme catalyst: S-carboxymethyl-L-cysteine synthase from Escherichia coli W₃₁₁₀;

DOI:10.1080/00021369.1989.10869692

upstream raw materials:

(R)-2-tert-Butoxycarbonylamino-3-((R)-2,3-dihydroxy-propylsulfanyl)-propionic acid tert-butyl ester

2-amino-3-chloropropanoic acid

rac-3-sulfanylpropane-1,2-diol

S-<(2RS)-2,3-Dihydroxypropyl>-N^α-Boc-Cys-OBu^t

Refernces

• 1、 Hussein, Waleed M.,Liu, Tzu-Yu,Maruthayanar, Pirashanthini,Mukaida, Saori,Moyle, Peter M.,Wells, James W.,Toth, Istvan,Skwarczynski, Mariusz. "Double conjugation strategy to incorporate lipid adjuvants into multiantigenic vaccines". . p. 2308 - 2321. Retrieved 2016/03/05.
• 2、 Tanaka,Shigematsu,Hori,Goto,Hashimoto,Tsud a,Okada. "Structure and synthesis of an immunoactive lipopeptide, WS1279, of microbial origin". . p. 1793 - 1795. Retrieved 2007/10/02.