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 …

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 …

Peptidyl inverse esters of p-methoxybenzoic acid: a novel class of potent inactivator of the serine proteases

J LYNAS, B WALKER - Biochemical Journal, 1997 - portlandpress.com
A series of novel synthetic peptides, containing a C-terminal β-amino alcohol linked to p-
methoxybenzoic acid via an ester linkage, have been prepared and tested as inhibitors …

The Synthesis of an Octapeptide Corresponding to a Sequence around the “Reactive Serine” of Chymotrypsin

HT Cheung, TS Murthy, ER Blout - Journal of the American …, 1964 - ACS Publications
was treated with/S-benzyl-L-aspartate9 in tetrahydro-furan-aqueous sodium hydroxide at pH
7-8 to give N-formylglycyl-^-benzyl-L-aspartate (III), mp 170,[a] D+ 6.7. NT rifluoroacetyl-O …

Serine proteinases mimics: hydrolytic activity of cyclic peptides which include a non-natural amino acid

H Ishida, K Donowaki, M Suga, K Shimose, K Ohkubo - Tetrahedron letters, 1995 - Elsevier
Serine Proteinases Mimics: Hydrolytic Activity of Cyclic Peptides Which Include a Non-natural
Amino Acid t Page 1 Tvrrnhrdrorl Lerreu, Vol. 36, No. 49. pp X987-8990, 1995 Elsevier Scmm …

A new stepwise synthesis of an octapeptide corresponding to a sequence around the “reactive” serine of chymotrypsin

DA Laufer, ER Blout - Journal of the American Chemical Society, 1967 - ACS Publications
The occurrence of a single reactive serine residue in several proteolytic enzymes has
indicated that the peptide sequences containing this reactiveserine are close to, or at, the …

Role of the S'Subsites in Serine Protease Catalysis. Active-Site Mapping of Rat Chymotrypsin, Rat Trypsin,. alpha.-Lytic Protease, and Cercarial Protease from …

V Schellenberger, CW Turck, WJ Rutter - Biochemistry, 1994 - ACS Publications
Revised Manuscript Received February 4, 1994® abstract: The S'subsite specificity of four
homologous serine proteases, rat chymotrypsin, rat trypsin,-lytic protease, and cercarial …

Kinetics and specificity of serine proteases in peptide synthesis catalyzed in organic solvents

H Gaertner, A Puigserver - European journal of biochemistry, 1989 - Wiley Online Library
Initial rates of peptide‐bond synthesis catalyzed by poly (ethylene glycol)‐modified
chymotrypsin in benzene were determined using high‐performance liquid chromatography …

Synthesis and catalytic properties of the pentapeptide, Thr-Ala-Cys-His-Asp

I Photaki, V Bardakos, AW Lake, G Lowe - Journal of the Chemical …, 1968 - pubs.rsc.org
The pentapeptide, Thr-Ala-Cys-His-Asp, has been synthesised by use of S-diphenylmethyl-
protected cysteine. The catalytic activity towards p-nitrophenyl acetate was comparable with …

N‐Hydroxy peptides as substrates for α‐chymotrypsin

A Bianco, D Kaiser, G Jung - The Journal of peptide research, 1999 - Wiley Online Library
An N‐hydroxylated peptide bond was found to be cleaved faster by an endopeptidase than
the corresponding peptide bond. This preferred enzymatic cleavage was detected during …