Total Synthesis of Laucysteinamide A, a Monomeric Congener of Somocystinamide A

Kimberly S Taylor; Chen Zhang; Evgenia Glukhov; William H Gerwick; Takashi L Suyama

doi:10.1021/acs.jnatprod.0c01317

Total Synthesis of Laucysteinamide A, a Monomeric Congener of Somocystinamide A

J Nat Prod. 2021 Mar 26;84(3):865-870. doi: 10.1021/acs.jnatprod.0c01317. Epub 2021 Feb 26.

Authors

Kimberly S Taylor¹, Chen Zhang², Evgenia Glukhov², William H Gerwick², Takashi L Suyama¹

Affiliations

¹ Department of Chemistry and Forensic Science, Waynesburg University, 51 W College Street, Waynesburg, Pennsylvania 15370, United States.
² Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093, United States.

PMID: 33635664
DOI: 10.1021/acs.jnatprod.0c01317

Abstract

Laucysteinamide A (4) is a marine natural product isolated from the cyanobacterium Caldora penicillata and contains structural motifs found in promising cancer drug leads. The first total synthesis of 4 and its analogues was achieved, which also enabled a concise formal synthesis of somocystinamide A (3), a dimeric congener of 4 that previously showed extremely potent antiproliferative activities. This work provides further insights on structure-activity relationships in this class of natural products.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Biological Products / chemistry
Biological Products / pharmacology
Cell Line, Tumor
Cyanobacteria / chemistry
Disulfides / chemistry*
Humans
Molecular Structure
Structure-Activity Relationship
Thiazoles / chemical synthesis*
Thiazoles / pharmacology

Substances

Antineoplastic Agents
Biological Products
Disulfides
Somocystinamide A
Thiazoles
laucysteinamide A

Supplementary concepts

Caldora penicillata