228402-71-9

Basic information

• Product Name: N-(3,3-dimethylbutyryl)-L-valyl-L-valine benzyl ester
• Synonyms: N-(3,3-dimethylbutyryl)-L-valyl-L-valine benzyl ester
• CAS NO: 228402-71-9
• Molecular Weight: 404.55
• Mol File: 228402-71-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(3,3-dimethylbutyryl)-L-valyl-L-valine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,3-dimethylbutyryl)-L-valyl-L-valine benzyl ester(228402-71-9)
• EPA Substance Registry System: N-(3,3-dimethylbutyryl)-L-valyl-L-valine benzyl ester(228402-71-9)

Safety Data

• Hazardous Substances Data: 228402-71-9(Hazardous Substances Data)

Upstream product

• 7065-46-5 3,3-dimethylbutanoic acid chloride 
• 72-18-4 L-valine 
• 21760-98-5 L-valine benzyl ester 
• 228402-73-1 N-(3,3-dimethylbutyryl)-L-valine 

Relevant articles and documents

Simplified pepstatins: Synthesis and evaluation of N-terminally modified analogues

The promising strategy of gastric ulcer healing with perorally administered epidermal growth factor (EGF) is so far strongly limited by the pepsinic degradation of this therapeutic polypeptide in the stomach. The incorporation of EGF in a bioadhesive polymer-pepsin inhibitor conjugate used as drug carrier matrix, however, might provide sufficient protection toward pepsinic degradation. The synthesis of appropriate pepsin inhibitors represents a prerequisite for the development of such polymer-inhibitor conjugates. The presented study demonstrates that modifications at the N- terminus of simplified analogues of pepstatin which can be synthesized in a simple and straight way result only in slight variations of the inhibitory activity. These analogues display only 10-fold reduced inhibitory activity, compared to pepstatin A, when bearing a greater N-terminal group like isovaleryl, Boc, or Cbz. Compounds which are substituted at the N-terminus by a shorter N-acyl group like propionyl or cyclopropylcarbonyl show further reduced activity (0.01, compared to pepstatin A). The presence of an amide or a urethane moiety at the N-terminus has no considerable effect on enzyme inhibition. Therefore, the N-terminus of these analogues is able to be modified forming a covalent bond to various bioadhesive polymers via a suitable functionality.