Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

Jieyan Lim; Venkaiah Chintalapudi; Haraldur G. Gudmundsson; Minh Tran; Alice Bernasconi; Araceli Blanco; Lijiang Song; Gregory L. Challis; Edward A. Anderson

doi:10.1021/acs.orglett.1c02650

Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

Jieyan Lim
, Venkaiah Chintalapudi
, Haraldur G. Gudmundsson
, Minh Tran
, Alice Bernasconi
, Araceli Blanco
, Lijiang Song
, Gregory L. Challis
, Edward A. Anderson

Faculty of Pharmaceutical Sciences

University of Iceland

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

Abstract

The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.

Original language	English
Pages (from-to)	7439-7444
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.1c02650
Publication status	Published - 1 Oct 2021

Bibliographical note

Funding Information: We thank the Agency for Science, Technology and Research (A*STAR) for a National Science Scholarship (J.L.), the Marie Skłodowska-Curie actions for an Individual Fellowship (V.C., GA No 702385), and the Leverhulme Trust for funding (H.G.G., RPG-2015-003). We are grateful to Jonathan Yong (University of Oxford) for his help in acquiring NMR spectra of 1 . E.A.A. thanks the EPSRC for additional support (EP/S013172/1). Publisher Copyright: ©

Access to Document

10.1021/acs.orglett.1c02650

Cite this

@article{cedc3c457c2a434d93fd8c15a04b4ac3,

title = "Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments",

abstract = "The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.",

author = "Jieyan Lim and Venkaiah Chintalapudi and Gudmundsson, \{Haraldur G.\} and Minh Tran and Alice Bernasconi and Araceli Blanco and Lijiang Song and Challis, \{Gregory L.\} and Anderson, \{Edward A.\}",

note = "Funding Information: We thank the Agency for Science, Technology and Research (A*STAR) for a National Science Scholarship (J.L.), the Marie Sk{\l}odowska-Curie actions for an Individual Fellowship (V.C., GA No 702385), and the Leverhulme Trust for funding (H.G.G., RPG-2015-003). We are grateful to Jonathan Yong (University of Oxford) for his help in acquiring NMR spectra of 1 . E.A.A. thanks the EPSRC for additional support (EP/S013172/1). Publisher Copyright: {\textcopyright}",

year = "2021",

month = oct,

day = "1",

doi = "10.1021/acs.orglett.1c02650",

language = "English",

volume = "23",

pages = "7439--7444",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

AU - Lim, Jieyan

AU - Chintalapudi, Venkaiah

AU - Gudmundsson, Haraldur G.

AU - Tran, Minh

AU - Bernasconi, Alice

AU - Blanco, Araceli

AU - Song, Lijiang

AU - Challis, Gregory L.

AU - Anderson, Edward A.

N1 - Funding Information: We thank the Agency for Science, Technology and Research (A*STAR) for a National Science Scholarship (J.L.), the Marie Skłodowska-Curie actions for an Individual Fellowship (V.C., GA No 702385), and the Leverhulme Trust for funding (H.G.G., RPG-2015-003). We are grateful to Jonathan Yong (University of Oxford) for his help in acquiring NMR spectra of 1 . E.A.A. thanks the EPSRC for additional support (EP/S013172/1). Publisher Copyright: ©

PY - 2021/10/1

Y1 - 2021/10/1

N2 - The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.

AB - The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.

UR - https://www.scopus.com/pages/publications/85115975981

U2 - 10.1021/acs.orglett.1c02650

DO - 10.1021/acs.orglett.1c02650

M3 - Article

C2 - 34494848

SN - 1523-7060

VL - 23

SP - 7439

EP - 7444

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

Abstract

Bibliographical note

Access to Document

Fingerprint

Cite this