A combined solid- and solution-phase approach provides convenient access to analogues of the calcium-dependent lipopeptide antibiotics

Organic & Biomolecular Chemistry
Peter 't HartNathaniel I Martin

Abstract

The calcium-dependent lipopeptide antibiotics represent a promising new class of antimicrobials for use in combating drug-resistant bacteria. At present, daptomycin is the only such lipopeptide used clinically and displays potent antimicrobial activity against a number of pathogenic Gram-positive bacteria. Given the increasing need for new antibiotics, practical synthetic access to unnatural analogues of daptomycin and related antimicrobial lipopeptides is of value. We here report an efficient synthetic route combining solid- and solution-phase techniques that allows for the rapid preparation of daptomycin analogues. Using this approach, four such analogues, including two enantiomeric variants, were synthesized and their antimicrobial activities and hydrolytic stabilities evaluated.

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Citations

Mar 12, 2016·Journal of Medicinal Chemistry·Laurens Hj KleijnNathaniel I Martin
May 13, 2014·Chemistry : a European Journal·Matthias De VleeschouwerAnnemieke Madder
Jan 31, 2015·Organic Letters·Chuda Raj LohaniScott D Taylor
Nov 2, 2015·Bioorganic & Medicinal Chemistry Letters·Chuda Raj LohaniScott D Taylor
Jan 3, 2018·Biopolymers·Ghufran BarnawiScott D Taylor
Jan 29, 2021·Organic & Biomolecular Chemistry·Ryan MoreiraScott D Taylor
Apr 11, 2019·The Journal of Organic Chemistry·Michael NodenScott D Taylor
Dec 25, 2019·The Journal of Organic Chemistry·Braden KraltScott D Taylor
Aug 27, 2019·The Journal of Organic Chemistry·Braden KraltScott D Taylor
Jul 21, 2020·Journal of Medicinal Chemistry·John A KarasTony Velkov
Nov 30, 2021·Angewandte Chemie·Ryan Moreira, Scott D Taylor

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