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Insights into the Biosynthetic Origin of 3-(3-Furyl)alanine in Stachylidium sp. 293 K04 Tetrapeptides

Author:
El Maddah, Fayrouz, Kehraus, Stefan, Nazir, Mamona, Almeida, Celso, König, Gabriele M.
Source:
Journal of natural products 2016 v.79 no.11 pp. 2838-2845
ISSN:
1520-6025
Subject:
Stachylidium, alanine, fungi, isotope labeling, peptides, phenylalanine, serotonin receptors, shikimate pathway, vasopressin receptors
Abstract:
The marine-sponge-derived fungus Stachylidium sp. 293 K04 produces the N-methylated peptides endolide A (1) and endolide B (2), showing affinity for the vasopressin receptor 1A and serotonin receptor 5HT₂B, respectively. Both peptides feature the rare amino acid 3-(3-furyl)alanine. Isotope labeling experiments, employing several ¹³C-enriched precursors, revealed that this unprecedented heterocyclic amino acid moiety in endolide A (1) is synthesized from a cyclic intermediate of the shikimate pathway, but not from phenylalanine. Two new tetrapeptide analogues, endolides C and D (3 and 4), were characterized, as well as the previously described hirsutide (5).
Agid:
5590303