82938-87-2

Upstream product

• 69875-06-5 N-(N-benzyloxycarbonyl-L-alanyl)-β-alanine methyl ester 
• 1142-20-7 N-Cbz-Ala 
• 65005-45-0 benzyloxycarbonylalanyl-β-alanine ethyl ester 

Downstream Products

• 111196-03-3 benzyloxycarbonylalanyl-β-alanyl-alanine p-nitroanilide 
• 82938-88-3 N-(N-benzyloxycarbonyl-L-alanyl)-β-alanyl-L-proline 
• 111196-10-2 3-carboxypropionylalanyl-β-alanyl-alanine p-nitroanilide 
• 82938-89-4 N-(N-benzyloxycarbonyl-L-alanyl)-β-alanyl-L-proline p-nitrophenyl ester 
• 82938-90-7 (S)-2-Methyl-3,6-dioxo-2,3,5,6,8,9-hexahydro-4H,7H-1,3a,6a-triaza-cyclopenta[e]azulene-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

ROLE OF AMINO ACID RESIDUES IN CHROMOGENIC SUBSTRATES CLEAVED BY PANCREATIC ELASTASE

Anionic chromogenic substrates, 3-carboxypropionyl tripeptide p-nitroanilides modified with glycine, β-alanine, alanine, leucine, and proline in positions P1, P2, and P3 were synthesized.The substrates were digested with pancreatic elastase and the values of Km, kcat, and kcat/Km were determined.Alanine plays a decisive role in position P1, substrates with glycine or β-alanine in this position are not cleaved.The substitution in P2 is dominant for proline; next follow alanine, leucine, and glycine.The substitution in P3 is the least specific one.

Cyclol Formation from Tripeptides containing β-Alanine

Attempts to synthesize stable tetrahedral intermediates (cyclols) from β-alanine containing precursors are described.Cyclization of N-(N-benzyloxycarbonyl-β-alanyl)-Phe-Pro-ONp gave N-(N-benzyloxycarbonyl-β-alanyl)-cyclo-(Phe-D-Pro).Cyclization of N-(N-benzyloxycarbonyl-Ala)-βAla-Pro-ONp and of N--Pro-ONp afforded the corresponding anhydrocyclols.The first example of an oxa-cyclol related to a ten membered cyclodepsitripeptide was synthesized by acylating cyclo-(βAla-Pro) with α-benzyloxypropionyl chloride followed by hydrogenolytic removal of the O-benzyl protecting group.