The structure of pepstatin.
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TLDR
Pepstatin gives mono-methyl ester by treatment of diazomethane and the di-acetyl derivative of the methyl ester is obtained by acetic anhydride and pyridine, and has no free basic function.Abstract:
The UV spectrum of pepstatin shows only end absorption. Strong absorptions centered at 1630cm\"1 and 1540cm\"1 in the infrared spectrum suggest that pepstatin is a kind of peptide. Pepstatin shows a negative reaction for ninhydrin, but positive for RydonSmith reagent. Pepstatin has no free basic function. It gives mono-methyl ester by treatment of diazomethane. The di-acetyl derivative of the methyl ester is obtained by acetic anhydride and pyridine. Acid hydrolysis of pepstatin in 6 N hydrochloric acid at 110°C for 27 hours gave two ninhydrin-positive products and another ma-read more
Citations
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Journal ArticleDOI
Pepstatin, a new pepsin inhibitor produced by agtinomygetes
Book ChapterDOI
Structures and activities of protease inhibitors of microbial origin.
TL;DR: The assay methods employed at the time of discovery of each inhibitor, special fermentation conditions, and methods for extraction and purification of the inhibitors are described in this chapter.
Journal ArticleDOI
Mode of inhibition of acid proteases by pepstatin.
TL;DR: It is suggested that the statyl residue is responsible for the unusual inhibitory capability of pepstatin and that statine is an analog of the previously proposed transition state for catalysis by pepsin and other acid proteases.
Journal ArticleDOI
Effect of pepstatin on acid proteases
TL;DR: It is indicated that a sufficient amount of pepstatin to inhibit pepsin remains in the gastric juice 60 minutes after oral administration, and pepStatin was shown to inhibit release of bound sialic acid from the mucous membrane.
References
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Journal ArticleDOI
A Rapid Permethylation of Glycolipid, and Polysaccharide Catalyzed by Methylsulfinyl Carbanion in Dimethyl Sulfoxide
TL;DR: It was undertaken to demonstrate the presence of various kinds of acyl residue in this solvent by ` hydroxylaminolysis' of the urinary glyco protein.
Journal ArticleDOI
Pepstatin, a new pepsin inhibitor produced by agtinomygetes
Journal ArticleDOI
Gas-liquid chromatography of trifluoroacetylated amino acid methyl esters.
A. Darbre,Ayesha Islam +1 more
Journal ArticleDOI
Advantages and limitations of the mass spectrometric sequence determination of permethylated oligopeptide derivatives.
TL;DR: The mass spectrometric sequence determination of O,N-permethylated oligopeptide derivatives can be extremely facile because their spectra consist principally of peaks arising from CO-NCH 3 cleavage.
Journal ArticleDOI
The Synthesis of O-Acetylhydroxy-α-amino Acids
Meir Wilchek,Abraham Patchornik +1 more