Late-Stage Functionalization of Peptides and Cyclopeptides Using Organozinc Reagents

被引：26

作者：

Leroux, Marcel ^{[1
]}

Vorherr, Thomas ^{[2
]}

Lewis, Ian ^{[2
]}

Schaefer, Michael ^{[2
]}

Koch, Guido ^{[2
]}

Karaghiosoff, Konstantin ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany

[2] Novartis Pharma AG, CH-4002 Basel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 24期

关键词：

cross-coupling; cyclopeptides; membrane permeability; organozinc; peptides; CATALYZED CROSS-COUPLINGS; ACIDIC HYDROGEN-ATOMS; ZINC REAGENTS; POSTSYNTHETIC MODIFICATION; ORAL BIOAVAILABILITY; BIOACTIVE PEPTIDES; HALIDES; DRUG; ARYL; ORGANOMETALLICS;

D O I：

10.1002/anie.201902454

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a new late-stage functionalization of small peptides and cyclopeptides relying on the Negishi cross-coupling of readily prepared iodotyrosine- or iodophenylalanine-containing peptides with aryl-, heteroaryl-, and alkylzinc pivalates or halides. In silico and in vitro determinations of membrane permeability parameters of the modified cyclopeptides showed that in most cases, the solubility was improved by the introduction of polar pyridyl units while the cell-membrane permeability was maintained.

引用

页码：8231 / 8234

页数：4

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