19647-70-2

Basic information

• Product Name: S-(acetamidomethyl)-L-cysteine
• Synonyms: S-(acetamidomethyl)-L-cysteine;(S-acetamidomethyl)cysteine;S-[(Acetylamino)methyl]-L-cysteine;28798-28-9 (Hydrochloride);Einecs 243-201-0;H-Cys(AcM)-OH·H2O S-AcetaMidoMethyl-L-cysteine Monohydrate;L-Cysteine, S-[(acetylamino)methyl]-
• CAS NO: 19647-70-2
• Molecular Formula: C₆H₁₂N₂O₃S
• Molecular Weight: 192.23608
• EINECS: 243-201-0
• Mol File: 19647-70-2.mol

Chemical Properties

• Boiling Point: 423.731 °C at 760 mmHg
• Flash Point: 210.065 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 1.33E-09mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: S-(acetamidomethyl)-L-cysteine(CAS DataBase Reference)
• NIST Chemistry Reference: S-(acetamidomethyl)-L-cysteine(19647-70-2)
• EPA Substance Registry System: S-(acetamidomethyl)-L-cysteine(19647-70-2)

Safety Data

• Hazardous Substances Data: 19647-70-2(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
S-(acetamidomethyl)-L-cysteine is used as a research tool for various mechanistic studies in the fields of chemistry and biochemistry. Its unique structure and properties make it valuable for understanding complex biological processes and interactions.
Used in Pharmaceutical Industry:
S-(acetamidomethyl)-L-cysteine is used as an intermediate product in the synthesis of pharmaceutical compounds. Its chemical properties allow it to be a key component in the development of new drugs and therapeutic agents.
Used in Chemical Industry:
S-(acetamidomethyl)-L-cysteine is used as a chemical intermediate in the production of various chemical products. Its versatility in chemical reactions makes it a valuable asset in the synthesis of a wide range of compounds.
Used in Biochemical Studies:
S-(acetamidomethyl)-L-cysteine is used as a biochemical research tool to investigate the role of sulfur-containing compounds in biological systems. Its presence in the structure of certain proteins and enzymes can provide insights into their functions and mechanisms of action.

InChI:InChI=1/C6H12N2O3S/c1-4(9)8-3-12-2-5(7)6(10)11/h5H,2-3,7H2,1H3,(H,8,9)(H,10,11)/t5-/m0/s1

Upstream product

• 52-90-4 L-Cysteine 
• 625-51-4 N-(hydroxymethyl)acetamide 
• 52-89-1 l-cysteine hydrochloride 
• 19746-37-3 N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine 
• 75893-05-9 H-Cys(Acm)(O)-OH 

Downstream Products

• 19746-37-3 N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine 
• 86060-81-3 S-[(acetylamino)methyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine 
• 38254-63-6 S-(2-hydroxyethylmercapto)-L-cysteine 
• 56-89-3 L-cystine 
• 54784-68-8 N-carbobenzoxy-L-S-(acetamidomethyl)cysteine 
• 82154-61-8 (R)-3-(Acetylamino-methylsulfanyl)-2-benzyloxycarbonylamino-propionic acid 4-nitro-phenyl ester 
• 144397-95-5 ZNHCysHisOMe 
• 86060-96-0 FmocCys(Acm)OPfp 

Relevant articles and documents

Disulfide bond formation using the silyl chloride-sulfoxide system for the synthesis of a cystine peptide

An efficient method for disulfide bond formation in peptides by the silyl chloride-sulfoxide system is described. Methyltrichlorosilane in trifluoroacetic acid, in the presence of diphenyl sulfoxide, is found to cleave various S-protecting groups of cysteine to form cystine directly within 10-30 min. No side reactions were observed with nucleophilic amino acids such as Met, His, or Tyr, except for Trp, under the reaction conditions of the silyl chloride-sulfoxide treatment. A chlorination of the indole moiety of unprotected Trp, rather than sulfur-sulfur bond formation, is a dominant reaction when the peptide containing unprotected Trp is treated with the chlorosilane-sulfoxide. However, the disulfide bond can be formed efficiently with no modification at the indole ring by treatment of the peptide having a formyl-protected Trp residue with the silyl chloride-sulfoxide system. The formyl group is removed by a brief treatment at basic pH without affecting the disulfide bond formed by the silyl chloride-sulfoxide treatment. This new disulfide bond forming reaction in trifluoroacetic acid is successfully applied to the syntheses of oxytocin, human brain natriuretic peptide, and somatostatin without any solubility problem.

STUDIES ON PEPTIDES. XCVI. BEHAVIOR OF S-ACETAMIDOMETHYLCYSTEINE SULFOXIDE UNDER DEPROTECTING CONDITIONS IN PEPTIDE SYNTHESIS

The sulfoxide of Boc-Cys(S-acetamidomethyl)-OH was prepared by oxidation with sodium perborate.Mercuric acetate and iodine failed to cleave the S-protecting group from sulfoxide.Hydrogen fluoride and methanesulfonic acid partially converted the sulfoxide to S-p-methoxyphenylcysteine in the presence of anisole.A reducing reagent, thiophenol, converted the sulfoxide to acetamidomethyl phenyl sulfide and Nα-Boc-S-(phenylthio)cysteine.Keywords - S-acetamidomethylcysteine sulfoxide; mercuric acetate treatment; iodine treatment; hydrogen fluoride treatment; methanesulfonic acid treatment; thiophenol treatment

N-t-butoxycarbonyl-S-lower alkanoylamidomethyl-cysteine and p-nitrophenyl esters

Novel protecting groups for peptides containing a cysteine residue. Process for the synthesis of peptides containing a cysteine residue wherein the mercapto function of the cysteine residue is protected by an acetamidomethyl radical or other labile blocking group. Novel intermediates useful in peptide synthesis.