Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support

TY - JOUR

T1 - Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support

AU - Oddo, Alberto

AU - Münzker, Lena

AU - Hansen, Paul Robert

PY - 2015/5/15

Y1 - 2015/5/15

N2 - A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented. (Chemical Equation Presented).

AB - A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented. (Chemical Equation Presented).

U2 - 10.1021/acs.orglett.5b01026

DO - 10.1021/acs.orglett.5b01026

M3 - Journal article

C2 - 25923311

SN - 1523-7060

VL - 17

SP - 2502

EP - 2505

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -