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Pyrroloindoline cyclization in tryptophan-containing cyclodipeptides mediated by an unprecedented indole C3 methyltransferase from Streptomyces sp. HPH0547

Author:
Li, Hongxia, Qiu, Yan, Guo, Canxiong, Han, Meng, Zhou, Yuyang, Feng, Yue, Luo, Shizhong, Tong, Yigang, Zheng, Guojun, Zhu, Shaozhou
Source:
Chemical communications 2019 v.55 no.58 pp. 8390-8393
ISSN:
1364-548X
Subject:
Streptomyces, alkaloids, biosynthesis, catalytic activity, dipeptides, methylation, methyltransferases, tryptophan
Abstract:
Diverse bioactive alkaloids with a tryptophan 2,5-diketopiperazine (DKP) core and an annulated structure forming a methylated pyrroloindoline–DKP assembly have been isolated from various microbial sources. However, little is known about their biosynthesis. In this study, a novel indole C3 methyltransferase from Streptomyces sp. HPH0547 was discovered and characterized. Structural elucidation of the products revealed that this enzyme catalyzed unique pyrroloindoline cyclization in tryptophan-containing cyclodipeptides. This is the first C3 methyltransferase reported to catalyze pyrroloindoline cyclization in cyclic dipeptides, which provides a feasible and simple method to access diverse alkaloids.
Agid:
6539554