23032-53-3

Usage

Chemical Properties

Crystalline

Upstream product

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

Downstream Products

• 953-18-4 S-benzyl-D-cysteine ethyl ester 
• 22911-80-4 N-(benzyloxycarbonyl)-S-benzyl-D-cysteine 
• 88243-77-0 (S)-(-)-2-amino-3-benzylthiopropan-1-ol 
• 873329-49-8 O-trimethylsilyl-S-benzyl-L-cysteine 
• 30134-76-0 (R)-(-)-2-hydroxy-3-benzylthiopropanoic acid 
• 119681-42-4 S-benzyl-N-(S-benzyl-N-benzyloxycarbonyl-D-cysteinyl)-L-cysteine ethyl ester 
• 55559-24-5 S-benzyl-N-(S-benzyl-N-benzyloxycarbonyl-D-cysteinyl)-L-cysteine 
• 7669-86-5 S-benzyl-N-(S-benzyl-D-cysteinyl)-L-cysteine 
• 349-46-2 S,S-cystine 
• 124775-73-1 S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-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 

Relevant academic research and scientific papers

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.

Versatile Synthesis of Stereospecifically Labelled D-Amino Acids via Labelled Aziridines - Preparation of (2R,3S)-- and (2R,3R)--Serine; (2S,2'S,3S,3'S)-- and (2S,2'S,3R,3'R)--Cystine; and (2S,3S)- and (2S,3R)--β-Chloroalanine

Stereospecifically β-labelled protected 2-carboxyaziridines 2, with the stereochemistry of a D-amino acid at C-2, have been prepared by a chemicoenzymic synthesis.Preparation of the labelled malates 5, by hydration of fumaric acid using the enzyme fumarase or by amination with aspartase followed by nitrosation, was followed by conversion into the isoserines 3, by a process involving Curtius rearrangement with retention of stereochemistry at the chirally labelled primary centre.Protection and ring closure gave the aziridines 2, which, on ring opening with the appropriate nucleophiles and deprotection, gave stereospecifically labelled samples of D-serine 16, D-cystine 20 and β-chloro-D-alanine 22.

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).