16597-46-9

Basic information

• Product Name: Cysteine,S-(phenylmethyl)-
• Synonyms: Alanine,3-(benzylthio)-, DL- (8CI); DL-Cysteine, S-(phenylmethyl)-; Alanine,3-[(phenylmethyl)thio]-; NSC 2527; S-Benzyl-DL-cysteine
• CAS NO: 16597-46-9
• Molecular Formula: C₁₀H₁₃NO₂S
• Molecular Weight: 211.2807
• Mol File: 16597-46-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 379.2°Cat760mmHg
• Flash Point: 183.2°C
• Density: 1.258g/cm³
• CAS DataBase Reference: Cysteine,S-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cysteine,S-(phenylmethyl)-(16597-46-9)
• EPA Substance Registry System: Cysteine,S-(phenylmethyl)-(16597-46-9)

Safety Data

• Hazardous Substances Data: 16597-46-9(Hazardous Substances Data)

Usage

General Description

Cysteine, S-(phenylmethyl)-, also known as phenylmethylation of cysteine, is a chemical compound with the formula C12H15NO3S. It is an amino acid derivative that contains a phenylmethyl side chain attached to the sulfur atom of cysteine. Cysteine,S-(phenylmethyl)- is often used in biochemistry and pharmaceutical research as a building block for the synthesis of peptides and proteins. It is also used in the production of various drugs, including antiviral and anticancer agents. Additionally, cysteine, S-(phenylmethyl)- has potential applications in the development of new therapeutic treatments due to its ability to modulate protein-protein interactions and enzyme activity. Overall, this chemical compound has important implications in the fields of medicine, drug discovery, and biochemistry.

Upstream product

• 100-53-8 phenylmethanethiol 
• 102830-49-9 N-tert-butyloxycarbonyl-(S)-benzyl-N-(tert-butyloxycarbonyl)-D-cysteine 
• 115355-23-2 S-(phenylmethyl)-D-cysteine ethyl ester hydrochloride 
• 5680-65-9 2-amino-3-(benzylthio)propionic acid 
• 3054-01-1 S-benzyl-L-cysteine 

Downstream Products

• 124775-73-1 S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-D-cysteine 
• 349-46-2 S,S-cystine 
• 7669-86-5 S-benzyl-N-(S-benzyl-D-cysteinyl)-L-cysteine 
• 55559-24-5 S-benzyl-N-(S-benzyl-N-benzyloxycarbonyl-D-cysteinyl)-L-cysteine 
• 119681-42-4 S-benzyl-N-(S-benzyl-N-benzyloxycarbonyl-D-cysteinyl)-L-cysteine ethyl ester 
• 873329-49-8 O-trimethylsilyl-S-benzyl-L-cysteine 
• 30134-76-0 (R)-(-)-2-hydroxy-3-benzylthiopropanoic acid 
• 88243-77-0 (S)-(-)-2-amino-3-benzylthiopropan-1-ol 
• 22911-80-4 N-(benzyloxycarbonyl)-S-benzyl-D-cysteine 
• 161512-71-6 S-Benzyl-N-acetyl-D-Cys 
• 19538-71-7 N-acetyl-S-benzyl-D,L-cysteine 
• 19542-77-9 N-acetyl-S-benzyl-L-cysteine 
• 921-01-7 D-cysteine 
• 495-69-2 Hippuric Acid 

Relevant articles and documents

Subtype-Specific Agonists for NMDA Receptor Glycine Binding Sites

A series of analogues based on serine as lead structure were designed, and their agonist activities were evaluated at recombinant NMDA receptor subtypes (GluN1/2A-D) using two-electrode voltage-clamp (TEVC) electrophysiology. Pronounced variation in subunit-selectivity, potency, and agonist efficacy was observed in a manner that was dependent on the GluN2 subunit in the NMDA receptor. In particular, compounds 15a and 16a are potent GluN2C-specific superagonists at the GluN1 subunit with agonist efficacies of 398% and 308% compared to glycine. This study demonstrates that subunit-selectivity among glycine site NMDA receptor agonists can be achieved and suggests that glycine-site agonists can be developed as pharmacological tool compounds to study GluN2C-specific effects in NMDA receptor-mediated neurotransmission.

ASYMMERTIC SYNTHESIS OF Β-SUBSTITUTED α-AMINO ACIDS VIA A CHIRAL Ni(II) COMPLEX OF DEHYDROALANINE

An efficient approach to the asymmetric synthesis of β-substituted (S)-alanines is describen.The chiral Ni(II) complex of a Schiff base derived from (S)-o-N-(N-benzylpropyl)aminobenzophenone (BBP) and glycine was treated with formaldehyde and sodium methoxide to give a corresponding (R)-serine complex which, in turn, was converted to the chiral Ni(II) dehydroalanine complex.Michael type base catalyzed addition of nucleophiles (including MeOH, Me2NH, PhCH2NH2, imidazole, PhSH, PhCH2SH,, malonic ester and benzylmagnesium chloride) produced a mixture of diastereoisomeric complexes with a 70-90percent excess of S,S (or L,L) isomers over the S,R (or L,D) ones.The cleavage of pure diastereoisomers with aqueous HCl gave, in good yields, β-substituted (S) (or L)-alanines and regenerated the chiral auxiliary (BBP).