17445-27-1

Basic information

• Product Name: (R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid
• Synonyms: (R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid
• CAS NO: 17445-27-1
• Molecular Weight: 354.427
• Mol File: 17445-27-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid(17445-27-1)
• EPA Substance Registry System: (R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid(17445-27-1)

Safety Data

• Hazardous Substances Data: 17445-27-1(Hazardous Substances Data)

Usage

General Description

"(R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid" is a chemical compound with the molecular formula C21H24N2O5S. It is a derivative of propanoic acid and contains a benzyl carbonyl group and a methyl sulfanyl group. (R)-2-[(S)-2-benzyloxycarbonylamino-4-methylsulfanylbytyrylamino]propanoic acid is a dipeptide derivative with a chiral center and is commonly used in pharmaceutical research and development. It has potential therapeutic applications in the treatment of various diseases and conditions, and its precise structure makes it a valuable tool in drug design and molecular targeting studies. The chemical properties and biological activities of this compound make it an important research target in the field of medicinal chemistry.

Upstream product

• 869772-05-4 benzyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate 
• 338-69-2 D-Alanine 
• 1152-62-1 Cbz-Met-OH 
• 14316-06-4 D-alanine methyl ester hydrochloride 

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.