Microwave-assisted solid-phase synthesis of side-chain to side-chain lactam-bridge cyclic peptides

被引：30

作者：

Tala, Srinivasa R. ^{[1
]}

Schnell, Sathya M. ^{[1
]}

Haskell-Luevano, Carrie ^{[1
]}

机构：

[1] Univ Minnesota, Dept Med Chem, Minneapolis, MN 55455 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2015年 / 25卷 / 24期

关键词：

Cyclic peptides; Microwave assisted synthesis; Lactam-bridge cyclic peptides; SHU9119; MTI I; CONFORMATIONAL-ANALYSIS; MELANOCORTIN RECEPTORS; MELANOTROPIN ANALOGS; BIOLOGICAL-ACTIVITY; ALPHA-MELANOTROPIN; AMINO-ACIDS; IN-VIVO; MT-II; DESIGN; SELECTIVITY;

D O I：

10.1016/j.bmcl.2015.10.095

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Side-chain to side-chain lactam-bridged cyclic peptides have been utilized as therapeutic agents and biochemical tools. Previous synthetic methods of these peptides need special reaction conditions, form side products and take longer reaction times. Herein, an efficient microwave-assisted synthesis of side-chain to side-chain lactam-bridge cyclic peptides SHU9119 and MTII is reported. The synthesis time and efforts are significantly reduced in the present method, without side product formation. The analytical and pharmacological data of the synthesized cyclic peptides are in accordance with the commercially obtained compounds. This new method could be used to synthesize other side-chain to side-chain lactam-bridge peptides and amenable to automation and extensive SAR compound derivatization. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5708 / 5711

页数：4

共 39 条

[1] POTENT AND PROLONGED ACTING CYCLIC LACTAM ANALOGS OF ALPHA-MELANOTROPIN - DESIGN BASED ON MOLECULAR-DYNAMICS [J].

ALOBEIDI, F ;

CASTRUCCI, AMD ;

HADLEY, ME ;

HRUBY, VJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (12) :2555-2561

[2] DESIGN OF A NEW CLASS OF SUPERPOTENT CYCLIC ALPHA-MELANOTROPINS BASED ON QUENCHED DYNAMIC SIMULATIONS [J].

ALOBEIDI, F ;

HADLEY, ME ;

PETTITT, BM ;

HRUBY, VJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3413-3416

[3] Structural mimicry of retroviral Tat proteins by constrained, β-hairpin peptidomimetics:: Ligands with high affinity and selectivity for viral TAR RNA regulatory elements [J].

Athanassiou, Z ;

Dias, RLA ;

Moehle, K ;

Dobson, N ;

Varani, G ;

Robinson, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (22) :6906-6913

[4] Sunflower Trypsin Inhibitor-1, Proteolytic Studies on a Trypsin Inhibitor Peptide and Its Analogs [J].

Colgrave, Michelle L. ;

Korsinczky, Michael J. L. ;

Clark, Richard J. ;

Foley, Fiona ;

Craik, David J. .

BIOPOLYMERS, 2010, 94 (05) :665-672

[5] High-Efficiency Solid Phase Peptide Synthesis (HE-SPPS) [J].

Collins, Jonathan M. ;

Porter, Keith A. ;

Singh, Sandeep K. ;

Vanier, Grace S. .

ORGANIC LETTERS, 2014, 16 (03) :940-943

[6] Melanocortin Antagonist Tetrapeptides with Minimal Agonist Activity at the Mouse Melanocortin-3 Receptor [J].

Doering, Skye R. ;

Todorovic, Aleksandar ;

Haskell-Luevano, Carrie .

ACS MEDICINAL CHEMISTRY LETTERS, 2015, 6 (02) :123-127

[7] Bioluminescence resonance energy transfer as a screening assay: Focus on partial and inverse agonism [J].

Elster, Lisbeth ;

Elling, Christian ;

Heding, Anders .

JOURNAL OF BIOMOLECULAR SCREENING, 2007, 12 (01) :41-49

[8] Discovery of a β-Hairpin Octapeptide, c[Pro-Arg-Phe-Phe-Dap-Ala-Phe-DPro], Mimetic of Agouti-Related Protein(87-132) [AGRP(87-132)] with Equipotent Mouse Melanocortin-4 Receptor (mMC4R) Antagonist Pharmacology [J].

Ericson, Mark D. ;

Wilczynski, Andrzej ;

Sorensen, Nicholas B. ;

Xiang, Zhimin ;

Haskell-Luevano, Carrie .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (11) :4638-4647

[9] Role of melanocortinergic neurons in feeding and the agouti obesity syndrome [J].

Fan, W ;

Boston, BA ;

Kesterson, RA ;

Hruby, VJ ;

Cone, RD .

NATURE, 1997, 385 (6612) :165-168

[10]

FELIX AM, 1988, INT J PEPT PROT RES, V32, P441

← 1 2 3 4 →