98398-16-4

Upstream product

• 115944-77-9 N-(N-benzyloxycarbonyl-L-methionyl)-L-glutamic acid diethyl ester 
• 16450-41-2 L-glutamic acid diethyl ester 
• 1152-62-1 Cbz-Met-OH 
• 869772-05-4 benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate 
• 56-86-0 L-glutamic acid 
• 63-68-3 L-methionine 

Downstream Products

• 14517-44-3 L-methionyl-L-glutamic acid 
• 116913-09-8 N-benzyloxycarbonyl-seryl=>tyrosyl=>methionyl=>glutamic acid 
• 114795-73-2 N-[N-(N-benzyloxycarbonyl-L-seryl)-L-methionyl]-L-glutamic acid 

Relevant academic research and scientific papers

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.