20695-98-1

Basic information

• Product Name: (2S)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-hydroxypropanoic acid
• Synonyms: (2S)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-hydroxypropanoic acid
• CAS NO: 20695-98-1
• Molecular Weight: 425.441
• Mol File: 20695-98-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-hydroxypropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-hydroxypropanoic acid(20695-98-1)
• EPA Substance Registry System: (2S)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-hydroxypropanoic acid(20695-98-1)

Safety Data

• Hazardous Substances Data: 20695-98-1(Hazardous Substances Data)

Upstream product

• 56-45-1 L-serin 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 850232-59-6 benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-(1H-indol-3-ylmethyl)-2-oxoethyl]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.