Evaluation of the Ser-His dipeptide, a putative catalyst of amide and ester hydrolysis

MJ MacDonald, LD Lavis, D Hilvert, SH Gellman - Organic letters, 2016 - ACS Publications
Efficient hydrolysis of amide bonds has long been a reaction of interest for organic chemists.
The rate constants of proteases are unmatched by those of any synthetic catalyst. It has …

[PDF][PDF] Catalyzed hydrolysis of amide and peptide bonds in proteins

J Steinhardt, CH Fugitt - J. Res. Natl Bur. Stand, 1942 - nvlpubs.nist.gov
The rates of hydrolysis by dilute acids of both a dissolved protein (egg albumin) and an
insoluble protein (wool) are shown to depend not only on the temperature and acidity but …

Neighboring-group participation of aldehydes and ketones in ester hydrolysis. Mechanism of hydrolysis of O-acetylsalicylaldehyde

JA Walder, RS Johnson, IM Klotz - Journal of the American …, 1978 - ACS Publications
The mechanism of hydrolysis of O-acetylsalicylaldehyde has been established by isotopic
tracer studies of the reac-tion carried out in H2lsO. The hydrate of the aldehyde operates as …

A Re-examination of two linear pentapeptides claimed to be serine protease mimics

AM Vandersteen, KD Janda - Journal of the American Chemical …, 1996 - ACS Publications
The synthesis, characterization, and kinetic study of two linear pentapeptides l-threonyl-l-
alanyl-l-seryl-l-histidyl-l-aspartic acid (TASHD) and l-seryl-γ-aminobutyryl-l-histidyl-γ …

Acid‐catalyzed hydrolysis of peptide‐amides in the solid state

PBW TEN KORTENAAR… - … Journal of Peptide …, 1990 - Wiley Online Library
The hydrolysis of peptide‐amides in the solid state at 4° due to the presence of residual
strong acid was investigated. It was found that even small molar excesses of these acids …

[19] Peptide aldehydes: Potent inhibitors of serine and cysteine proteases

RC Thompson - Methods in Enzymology, 1977 - Elsevier
Publisher Summary The peptide acids generated by protease-catalyzed hydrolysis of
proteins are generally good inhibitors of the enzymes that produce them. In the past few …

Specific cleavage of peptides containing an aspartic acid (. beta.-hydroxamic acid) residue

JK Blodgett, GM Loudon, KD Collins - Journal of the American …, 1985 - ACS Publications
Peptides containing the aspartyl d-hydroxamic acid residue are cleaved specifically at the
carboxyl side of this residue at pH values> 6. The cleavage occurs by attack of both the …

Catalysis in peptide synthesis

M Bodanszky - Journal of protein chemistry, 1985 - Springer
Enzyme catalyzed formation of peptide bonds reached practical significance in partial
syntheses such as the conversion of pork insulin to human insulin. Catalysis is important …

Fast hydrolysis of an aliphatic amide at neutral pH and ambient temperature. A peptidase model

FM Menger, M Ladika - Journal of the American Chemical Society, 1988 - ACS Publications
An intramolecular-catalyzed cleavage of an aliphatic amide under biological conditions
(ambient temperature, neutral pH, absence of alien transition metals) was found to occur …

[17] Reaction of serine proteases with aza-amino acid and aza-peptide derivatives

JC Powers, BF Gupton - Methods in enzymology, 1977 - Elsevier
Publisher Summary Aza-amino acid residues are analogs of amino acids in which the α-CH
has been replaced by a nitrogen atom. This substitution has a profound effect on the …