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Issue 3, 2019
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Isolation and characterization of tambjamine MYP1, a macrocyclic tambjamine analogue from marine bacterium Pseudoalteromonas citrea

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Abstract

Tambjamines are natural products that consist of a conserved bipyrrole core functionalized with different imines giving rise to many derivatives. The core structure of tambjamines allows ion coordination through the nitrogen atoms, which is a key aspect in many of their observed antimicrobial, anticancer, and antimalarial bioactivities. Minor variances in the compound structure have a considerable impact on the potency of these activities, so identifying new analogues is valuable for maximizing tambjamine biological potential. In this work, we describe the isolation and structure elucidation of the first naturally occurring macrocyclized tambjamine, tambjamine MYP1, from the marine microbe Pseudoalteromonas citrea. We also compare the apparent pKa of cyclic and linear tambjamine analogues and discuss how structural strain may effect the compound's ion coordination abilities.

Graphical abstract: Isolation and characterization of tambjamine MYP1, a macrocyclic tambjamine analogue from marine bacterium Pseudoalteromonas citrea

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Article information


Submitted
01 Feb 2019
Accepted
28 Feb 2019
First published
01 Mar 2019

Med. Chem. Commun., 2019,10, 478-483
Article type
Research Article

Isolation and characterization of tambjamine MYP1, a macrocyclic tambjamine analogue from marine bacterium Pseudoalteromonas citrea

K. J. Picott, J. A. Deichert, E. M. deKemp, G. Schatte, F. Sauriol and A. C. Ross, Med. Chem. Commun., 2019, 10, 478
DOI: 10.1039/C9MD00061E

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