Total Synthesis of Marformycins A and D

Avraz F. Anwar; Yassin M. Elbatrawi; David Degen; Richard H. Ebright; Juan R. Del Valle

doi:10.1021/acs.orglett.4c04013

Total Synthesis of Marformycins A and D

Avraz F. Anwar, Yassin M. Elbatrawi, David Degen, Richard H. Ebright, Juan R. Del Valle

Waksman Institute of Microbiology

Rutgers, The State University

Research output: Contribution to journal › Article › peer-review

Abstract

We report the synthesis of the antimicrobial cyclodepsipeptides marformycin A (1) and marformycin D (2) using a solid-phase approach. A scalable solution-phase synthesis of the γ-hydroxypiperazic acid subunit in 2, starting from cis-hydroxyproline, is also described. Structural analysis of 1 and its Leu-epi congener demonstrates conformational differences that may underlie their divergent antimicrobial activities. The described approach enables further development of conformation-activity relationships within this class of depsipeptide natural products.

Original language	American English
Pages (from-to)	10056-10060
Number of pages	5
Journal	Organic letters
Volume	26
Issue number	46
DOIs	https://doi.org/10.1021/acs.orglett.4c04013
State	Published - Nov 22 2024

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.4c04013

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abstract = "We report the synthesis of the antimicrobial cyclodepsipeptides marformycin A (1) and marformycin D (2) using a solid-phase approach. A scalable solution-phase synthesis of the γ-hydroxypiperazic acid subunit in 2, starting from cis-hydroxyproline, is also described. Structural analysis of 1 and its Leu-epi congener demonstrates conformational differences that may underlie their divergent antimicrobial activities. The described approach enables further development of conformation-activity relationships within this class of depsipeptide natural products.",

author = "Anwar, {Avraz F.} and Elbatrawi, {Yassin M.} and David Degen and Ebright, {Richard H.} and {Del Valle}, {Juan R.}",

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AU - Anwar, Avraz F.

AU - Elbatrawi, Yassin M.

AU - Degen, David

AU - Ebright, Richard H.

AU - Del Valle, Juan R.

PY - 2024/11/22

Y1 - 2024/11/22

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AB - We report the synthesis of the antimicrobial cyclodepsipeptides marformycin A (1) and marformycin D (2) using a solid-phase approach. A scalable solution-phase synthesis of the γ-hydroxypiperazic acid subunit in 2, starting from cis-hydroxyproline, is also described. Structural analysis of 1 and its Leu-epi congener demonstrates conformational differences that may underlie their divergent antimicrobial activities. The described approach enables further development of conformation-activity relationships within this class of depsipeptide natural products.

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JO - Organic letters

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ER -

Total Synthesis of Marformycins A and D

Abstract

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