S-(Acetamidomethyl)-L-cysteine

Base Information

• Chemical Name: S-(Acetamidomethyl)-L-cysteine
• CAS No.: 19647-70-2
• Molecular Formula: C6H12N2O3S
• Molecular Weight: 192.239
• Hs Code.: 2930909090
• European Community (EC) Number: 243-201-0
• UNII: SY9A2W0W25
• Nikkaji Number: J82.884J
• Wikidata: Q27459003
• Mol file: 19647-70-2.mol

Synonyms:(S-acetamidomethyl)cysteine;(S-acetamidomethyl)cysteine hydrochloride;S-acetamidomethyl-cysteine;SAM-cysteine

Chemical Property of S-(Acetamidomethyl)-L-cysteine

Chemical Property:

• Vapor Pressure: 1.33E-09mmHg at 25°C
• Refractive Index: 1.549
• Boiling Point: 423.731 °C at 760 mmHg
• Flash Point: 210.065 °C
• PSA: 126.95000
• Density: 1.27 g/cm³
• LogP: 0.25200
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 192.05686342
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

99% ^*data from raw suppliers

H-Cys(Acm)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of S-(Acetamidomethyl)-L-cysteine

There total 6 articles about S-(Acetamidomethyl)-L-cysteine 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: 79.0%

N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine (19746-37-3) → L-cystine (56-89-3) + S-acetamidomethyl-L-cysteine (19647-70-2)

Guidance literature:

With Methyltrichlorosilane; 1,1'-sulfinylbisbenzene; trifluoroacetic acid; at 4 ℃; for 0.166667h; Product distribution; Mechanism; var. reaction times, silyl chlorides and sulfoxides; other S-protected cystine-peptides;

DOI:10.1021/ja00037a015

Reference yield: 21.0%

H-Cys(Acm)(O)-OH (75893-05-9) → L-Cysteine (52-90-4) + L-Cysteic acid (498-40-8,3024-83-7) + L-cystine (56-89-3) + S-acetamidomethyl-L-cysteine (19647-70-2)

Guidance literature:

With ammonia; sodium; for 0.00277778h; Product distribution;

Reference yield:

l-cysteine hydrochloride (52-89-1) + N-(hydroxymethyl)acetamide (625-51-4) → S-acetamidomethyl-L-cysteine (19647-70-2)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1002/hlca.19740570215

upstream raw materials:

L-Cysteine

N-(hydroxymethyl)acetamide

l-cysteine hydrochloride

N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine

Downstream raw materials:

N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine

FmocCys(Acm)OPfp

ZNHCysHisOMe

(R)-3-(Acetylamino-methylsulfanyl)-2-benzyloxycarbonylamino-propionic acid 4-nitro-phenyl ester

Refernces

• 1、 Marbach,Rudinger. "Synthesis of [2 p fluorophenylalanine]oxytocin and its desamino analogue using the S acetamidomethyl protecting group". . p. 403 - 414. Retrieved 1974.
• 2、 Akaji, Kenichi,Tatsumi, Tadashi,Yoshida, Makoto,Kimura, Tooru,Fujiwara, Yoichi,Kiso, Voshiaki. "Disulfide bond formation using the silyl chloride-sulfoxide system for the synthesis of a cystine peptide". . p. 4137 - 4143. Retrieved 2007/10/02.
• 3、 -. "N-t-butoxycarbonyl-S-lower alkanoylamidomethyl-cysteine and p-nitrophenyl esters". . . Retrieved 2008/06/13.