BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY

GROEGER C, Wenzel H, Tschesche H (1994)
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH 44(2): 166-172.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
GROEGER, C; Wenzel, HerbertUniBi; Tschesche, HaraldUniBi
Einrichtung
Fakultät für Chemie > Biochemie I
Abstract / Bemerkung
Structural variants of BPTI were synthesized en route an enzymatic-chemical semisynthesis. The P-1-P-2 amide bond of the inhibitor molecule, which, as donor, contributes a hydrogen bond towards trypsin in the enzyme-inhibitor complex, was replaced by either a ketomethylene function or an ester bond yielding molecules with inhibitory activity. The two backbone-mutated BPTI derivatives showed increased dissociation constants of their respective trypsin complexes, obviously due to the lack of a single hydrogen-bond interaction in the enzyme-inhibitor complex. (C) Munksgaard 1994.
Stichworte
PEPTIDE; PEPTIDE BACKBONE; ENZYMATIC SEMISYNTHESIS; BPTI; DEPSIPEPTIDE; TRYPSIN INHIBITOR; ISOSTERE
Erscheinungsjahr
1994
Zeitschriftentitel
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH
Band
44
Ausgabe
2
Seite(n)
166-172
ISSN
0367-8377
Page URI
https://pub.uni-bielefeld.de/record/1642944

Zitieren

GROEGER C, Wenzel H, Tschesche H. BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH. 1994;44(2):166-172.
GROEGER, C., Wenzel, H., & Tschesche, H. (1994). BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 44(2), 166-172.
GROEGER, C, Wenzel, Herbert, and Tschesche, Harald. 1994. “BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY”. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH 44 (2): 166-172.
GROEGER, C., Wenzel, H., and Tschesche, H. (1994). BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH 44, 166-172.
GROEGER, C., Wenzel, H., & Tschesche, H., 1994. BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 44(2), p 166-172.
C. GROEGER, H. Wenzel, and H. Tschesche, “BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY”, INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, vol. 44, 1994, pp. 166-172.
GROEGER, C., Wenzel, H., Tschesche, H.: BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH. 44, 166-172 (1994).
GROEGER, C, Wenzel, Herbert, and Tschesche, Harald. “BPTI BACKBONE VARIANTS AND IMPLICATIONS FOR INHIBITORY ACTIVITY”. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH 44.2 (1994): 166-172.

7 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Probing Backbone Hydrogen Bonds in Proteins by Amide-to-Ester Mutations.
Sereikaitė V, Jensen TMT, Bartling CRO, Jemth P, Pless SA, Strømgaard K., Chembiochem 19(20), 2018
PMID: 30073762
Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides.
Thongyoo P, Roqué-Rosell N, Leatherbarrow RJ, Tate EW., Org Biomol Chem 6(8), 2008
PMID: 18385853
Conformational change from antiparallel beta-sheet to alpha-helix in a series of depsipeptide, -(Leu-Leu-Lac)(n)-: syntheses, spectroscopic studies, and crystal structures of Boc-Leu-Lac-OEt and Boc-(Leu-Leu-Lac)(n)-OEt (n = 1, 2).
Oku H, Yamada K, Katakai R., Biopolymers 89(4), 2008
PMID: 18067154
Immobilized protease-assisted synthesis of engineered cysteine-knot microproteins.
Thongyoo P, Jaulent AM, Tate EW, Leatherbarrow RJ., Chembiochem 8(10), 2007
PMID: 17526063
Amide-to-E-olefin versus amide-to-ester backbone H-bond perturbations: Evaluating the O-O repulsion for extracting H-bond energies.
Fu Y, Gao J, Bieschke J, Dendle MA, Kelly JW., J Am Chem Soc 128(50), 2006
PMID: 17165703
Contribution of peptide bonds to inhibitor-protease binding: crystal structures of the turkey ovomucoid third domain backbone variants OMTKY3-Pro18I and OMTKY3-psi[COO]-Leu18I in complex with Streptomyces griseus proteinase B (SGPB) and the structure of the free inhibitor, OMTKY-3-psi[CH2NH2+]-Asp19I.
Bateman KS, Huang K, Anderson S, Lu W, Qasim MA, Laskowski M, James MN., J Mol Biol 305(4), 2001
PMID: 11162096
Probing intermolecular backbone H-bonding in serine proteinase-protein inhibitor complexes.
Lu W, Randal M, Kossiakoff A, Kent SB., Chem Biol 6(7), 1999
PMID: 10381402
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