99094-87-8

Basic information

• Product Name: (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-methylbutanoic acid
• Synonyms: (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-methylbutanoic acid
• CAS NO: 99094-87-8
• Molecular Weight: 379.413
• Mol File: 99094-87-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-methylbutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-methylbutanoic acid(99094-87-8)
• EPA Substance Registry System: (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-methylbutanoic acid(99094-87-8)

Safety Data

• Hazardous Substances Data: 99094-87-8(Hazardous Substances Data)

Upstream product

• 4070-48-8 L-Valine methyl ester 
• 2650-64-8 Cbz-L-Gln 
• 14317-84-1 N-(N²-benzyloxycarbonyl-L-glutaminyl)-L-valine methyl ester 
• 850232-63-2 benzyl N-[(1S)-4-amino-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-4-oxobutyl]carbamate 
• 72-18-4 L-valine 
• 7763-16-8 N²-benzyloxycarbonyl-L-glutamine-(4-nitro-phenyl ester) 

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.