Zelkovamycins B–E, cyclic octapeptides containing rare amino acid residues from an endophytic Kitasatospora sp

Xiaomeng Hao; Jiaqing Yu; Yujia Wang; Jack A. Connolly; Yufeng Liu; Yuqin Zhang; Liyan Yu; Shan Cen; Rebecca J. M. Goss; Maoluo Gan

doi:10.1021/acs.orglett.0c03565

Zelkovamycins B–E, cyclic octapeptides containing rare amino acid residues from an endophytic Kitasatospora sp

Xiaomeng Hao, Jiaqing Yu, Yujia Wang, Jack A. Connolly, Yufeng Liu, Yuqin Zhang, Liyan Yu, Shan Cen, Rebecca J. M. Goss, Maoluo Gan

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

Abstract

Four unusual cyclopeptides, zelkovamycins B–E (1–4), were isolated from an endophytic Kitasatospora sp. Zelkovamycin B was featured by an unprecedented 3-methyl-5-hydroxypyrrolidine-2,4-dione ring system linked to the cyclopeptide skeleton. Their structures and full configurations were established by spectroscopic analysis, Marfey’s method, and NMR calculations. A plausible biosynthetic pathway for zelkovamycins was proposed based on gene cluster analysis. Zelkovamycin E displayed potent inhibitory activity against H1N1 influenza A virus.

Original language	English
Journal	Organic Letters
Volume	Articles ASAP
Early online date	20 Nov 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c03565
Publication status	E-pub ahead of print - 20 Nov 2020

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@article{dc9ccef1f9da4925981d86460bc1d368,

title = "Zelkovamycins B–E, cyclic octapeptides containing rare amino acid residues from an endophytic Kitasatospora sp",

abstract = "Four unusual cyclopeptides, zelkovamycins B–E (1–4), were isolated from an endophytic Kitasatospora sp. Zelkovamycin B was featured by an unprecedented 3-methyl-5-hydroxypyrrolidine-2,4-dione ring system linked to the cyclopeptide skeleton. Their structures and full configurations were established by spectroscopic analysis, Marfey{\textquoteright}s method, and NMR calculations. A plausible biosynthetic pathway for zelkovamycins was proposed based on gene cluster analysis. Zelkovamycin E displayed potent inhibitory activity against H1N1 influenza A virus.",

author = "Xiaomeng Hao and Jiaqing Yu and Yujia Wang and Connolly, {Jack A.} and Yufeng Liu and Yuqin Zhang and Liyan Yu and Shan Cen and Goss, {Rebecca J. M.} and Maoluo Gan",

year = "2020",

month = nov,

day = "20",

doi = "10.1021/acs.orglett.0c03565",

language = "English",

volume = "Articles ASAP",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - Zelkovamycins B–E, cyclic octapeptides containing rare amino acid residues from an endophytic Kitasatospora sp

AU - Hao, Xiaomeng

AU - Yu, Jiaqing

AU - Wang, Yujia

AU - Connolly, Jack A.

AU - Liu, Yufeng

AU - Zhang, Yuqin

AU - Yu, Liyan

AU - Cen, Shan

AU - Goss, Rebecca J. M.

AU - Gan, Maoluo

PY - 2020/11/20

Y1 - 2020/11/20

N2 - Four unusual cyclopeptides, zelkovamycins B–E (1–4), were isolated from an endophytic Kitasatospora sp. Zelkovamycin B was featured by an unprecedented 3-methyl-5-hydroxypyrrolidine-2,4-dione ring system linked to the cyclopeptide skeleton. Their structures and full configurations were established by spectroscopic analysis, Marfey’s method, and NMR calculations. A plausible biosynthetic pathway for zelkovamycins was proposed based on gene cluster analysis. Zelkovamycin E displayed potent inhibitory activity against H1N1 influenza A virus.

AB - Four unusual cyclopeptides, zelkovamycins B–E (1–4), were isolated from an endophytic Kitasatospora sp. Zelkovamycin B was featured by an unprecedented 3-methyl-5-hydroxypyrrolidine-2,4-dione ring system linked to the cyclopeptide skeleton. Their structures and full configurations were established by spectroscopic analysis, Marfey’s method, and NMR calculations. A plausible biosynthetic pathway for zelkovamycins was proposed based on gene cluster analysis. Zelkovamycin E displayed potent inhibitory activity against H1N1 influenza A virus.

U2 - 10.1021/acs.orglett.0c03565

DO - 10.1021/acs.orglett.0c03565

M3 - Article

SN - 1523-7060

VL - Articles ASAP

JO - Organic Letters

JF - Organic Letters

ER -

Zelkovamycins B–E, cyclic octapeptides containing rare amino acid residues from an endophytic Kitasatospora sp

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