Head-to-tail cyclized cystine-knot peptides by a combined recombinant and chemical route of synthesis

被引：24

作者：

Avrutina, Olga ^{[1
]}

Schmoldt, Hans-Ulrich ^{[1
,5
]}

Gabrijelcic-Geiger, Dusica ^{[3
]}

Wentzel, Alexander ^{[4
]}

Frauendorf, Holm ^{[2
]}

Sommerhoff, Christian P. ^{[3
]}

Diederichsen, Ulf ^{[2
]}

Kolmar, Harald ^{[1
]}

机构：

[1] Tech Univ Darmstadt, Inst Organ Chem & Biochem, D-64287 Darmstadt, Germany

[2] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

[3] Ludwig Maximillians Univ Klinikum, Klin Chem & Klin Biochem Abt, D-80336 Munich, Germany

[4] Selecore GmbH, D-37079 Gottingen, Germany

[5] Nascacell Technol AG, D-81377 Munich, Germany

来源：

CHEMBIOCHEM | 2008年 / 9卷 / 01期

关键词：

cyclic peptides; cystine knot miniproteins; hydrazones; inhibitors; macrocyclization; protein modifications;

D O I：

10.1002/cbic.200700452

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Backbone cyclization of recombinantly produced cystine knot peptides, resulting in correctly folded macrocyclic disulfide-bridged peptides, is reported. It does not require protecting groups, takes place in aqueous solution, and is devoid of racemization and solubility problems. Scaling up to production of multimilligram amounts of iminocyclotides seems feasible. The resulting iminocyclotides are biologically active proteinase inhibitors - imino-cyclo-McoEe-TIKKV was identified as the most potent proteinaceous inhibitor of human mast cell tryptase known. (Figure Presented) © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：33 / 37

页数：5

共 5 条

[1] Chemical synthesis of a homoserine-mutant of the antibacterial, head-to-tail cyclized protein AS-48 by α-ketoacid-hydroxylamine (KAHA) ligation
Rohrbacher, Florian
Zwicky, Andre
Bode, Jeffrey W.
CHEMICAL SCIENCE, 2017, 8 (05) : 4051 - 4055
[2] A Series of Novel Bioactive Cyclic Peptides: Synthesis by Head-to-Tail Cyclization Approach, Antimicrobial Activity and Molecular Docking Studies
Tivari, Sunil R.
Kokate, Siddhant V.
Sobhia, Elizabeth M.
Kumar, Siva G.
Shelar, Uttam B.
Jadeja, Yashwantsinh S.
CHEMISTRYSELECT, 2022, 7 (27):
[3] Preparation of head-to-tail cyclic peptides via side-chain attachment: Implications for library synthesis
Romanovskis, P
Spatola, AF
JOURNAL OF PEPTIDE RESEARCH, 1998, 52 (05): : 356 - 374
[4] Methionine anchoring applied to the solid-phase synthesis of lysine-containing 'head-to-tail' cyclic peptides
Joseph C. Kappel
George Barany
Letters in Peptide Science, 2003, 10 : 119 - 125
[5] Methionine anchoring applied to the solid-phase synthesis of lysine-containing 'head-to-tail' cyclic peptides
Kappel, JC
Barany, G
LETTERS IN PEPTIDE SCIENCE, 2003, 10 (02): : 119 - 125

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