886981-35-7

Basic information

• Product Name: 2((S)-2-benzyloxycarbonylamino-4-methylsulfanylbutyrylamino)propanoic acid
• Synonyms: 2((S)-2-benzyloxycarbonylamino-4-methylsulfanylbutyrylamino)propanoic acid
• CAS NO: 886981-35-7
• Molecular Weight: 354.427
• Mol File: 886981-35-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2((S)-2-benzyloxycarbonylamino-4-methylsulfanylbutyrylamino)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2((S)-2-benzyloxycarbonylamino-4-methylsulfanylbutyrylamino)propanoic acid(886981-35-7)
• EPA Substance Registry System: 2((S)-2-benzyloxycarbonylamino-4-methylsulfanylbutyrylamino)propanoic acid(886981-35-7)

Safety Data

• Hazardous Substances Data: 886981-35-7(Hazardous Substances Data)

Upstream product

• 1152-62-1 Cbz-Met-OH 
• 869772-05-4 benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate 
• 302-72-7 rac-Ala-OH 

Downstream Products

• 886981-45-9 benzyl N-[(S)-1-(2-benzotriazol-1-yl-1-methyl-2-oxoethylcarbamoyl)-3-methylsulfanylpropyl]carbamate 

Relevant articles and documents

The efficient preparation of di- and tripeptides by coupling N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles with unprotected amino acids

N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles 2 and N-protected peptidoylbenzotriazoles 6 are coupled in aqueous acetonitrile solution with free amino acids or dipeptides to prepare: (i) 22 chirally pure dipeptides 5a-v (in an average yield of 82%) from N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles 2 and unprotected amino acids, (ii) five chiral tripeptides 7a-e (in an average yield of 75%) from N-protected peptidoylbenzotriazoles 6 and unprotected amino acids, (iii) one chiral tripeptide 7g (62%) from N-(Cbz- or Fmoc-α- aminoacyl)benzotriazole 2a and the free dipeptide 8. In all, N-(Cbz- or Fmoc-α-aminoacyl)benzotriazole derivatives of 17 of the 20 naturally occurring amino acids were used, including those containing the following unprotected side chain functionalities: alcoholic -OH (Ser), indole -NH (Trp), imidazole -NH, phenolic -OH (Tyr), -CONH2 (Gln, Asn), -SH (Cys), -CO2H (Glu, Asp), and -S-S (Cystine). Support for the complete retention of chirality was obtained by parallel experiments involving D-Ala, L-Ala, and DL-Ala for the preparation of di- and tripeptides. This and other evidence for chiral integrity was supported by NMR and HPLC analyses. Georg Thieme Verlag Stuttgart.