A general scheme for synthesis of substrate-based polyketide labels for acyl carrier proteins

Erick K. Leggans; David L. Akey; Janet L. Smith; Robert A. Fecik

doi:10.1016/j.bmcl.2010.05.089

A general scheme for synthesis of substrate-based polyketide labels for acyl carrier proteins

Erick K. Leggans
, David L. Akey
, Janet L. Smith
, Robert A. Fecik

Medicinal Chemistry

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

3 Scopus citations

Abstract

A general strategy to enzymatically label acyl carrier proteins (ACPs) of polyketide synthases has been developed. Incorporation of a chloromethyl ketone or vinyl ketone moiety into polyketide chain elongation intermediate mimics allows for the synthesis of CoA adducts. These CoA adducts undergo enzymatic reaction with Sfp, a phosphopantetheinyl transferase, to afford labeled CurB carrier proteins.

Original language	English (US)
Pages (from-to)	5939-5942
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2010.05.089
State	Published - Oct 1 2010

Bibliographical note

Funding Information:
The authors thank Liangcai Gu and David Sherman for plasmid pET28b::CurB encoding CurB, K. R. Noon (Biomedical Mass Spectrometry Facility, University of Michigan) for assistance with LC–MS, and Jamie Razelun for preparation of CurB. Financial support from NIH DK-42303 (to J.L.S.) and NIH GM081544-01 (to J.L.S. and R.A.F.) is gratefully acknowledged.

Keywords

Acyl carrier proteins
Biosynthesis
Labels
Polyketides

Publisher link

10.1016/j.bmcl.2010.05.089

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title = "A general scheme for synthesis of substrate-based polyketide labels for acyl carrier proteins",

abstract = "A general strategy to enzymatically label acyl carrier proteins (ACPs) of polyketide synthases has been developed. Incorporation of a chloromethyl ketone or vinyl ketone moiety into polyketide chain elongation intermediate mimics allows for the synthesis of CoA adducts. These CoA adducts undergo enzymatic reaction with Sfp, a phosphopantetheinyl transferase, to afford labeled CurB carrier proteins.",

keywords = "Acyl carrier proteins, Biosynthesis, Labels, Polyketides",

author = "Leggans, \{Erick K.\} and Akey, \{David L.\} and Smith, \{Janet L.\} and Fecik, \{Robert A.\}",

note = "Funding Information: The authors thank Liangcai Gu and David Sherman for plasmid pET28b::CurB encoding CurB, K. R. Noon (Biomedical Mass Spectrometry Facility, University of Michigan) for assistance with LC–MS, and Jamie Razelun for preparation of CurB. Financial support from NIH DK-42303 (to J.L.S.) and NIH GM081544-01 (to J.L.S. and R.A.F.) is gratefully acknowledged. ",

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doi = "10.1016/j.bmcl.2010.05.089",

language = "English (US)",

volume = "20",

pages = "5939--5942",

journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - A general scheme for synthesis of substrate-based polyketide labels for acyl carrier proteins

AU - Leggans, Erick K.

AU - Akey, David L.

AU - Smith, Janet L.

AU - Fecik, Robert A.

N1 - Funding Information: The authors thank Liangcai Gu and David Sherman for plasmid pET28b::CurB encoding CurB, K. R. Noon (Biomedical Mass Spectrometry Facility, University of Michigan) for assistance with LC–MS, and Jamie Razelun for preparation of CurB. Financial support from NIH DK-42303 (to J.L.S.) and NIH GM081544-01 (to J.L.S. and R.A.F.) is gratefully acknowledged.

PY - 2010/10/1

Y1 - 2010/10/1

N2 - A general strategy to enzymatically label acyl carrier proteins (ACPs) of polyketide synthases has been developed. Incorporation of a chloromethyl ketone or vinyl ketone moiety into polyketide chain elongation intermediate mimics allows for the synthesis of CoA adducts. These CoA adducts undergo enzymatic reaction with Sfp, a phosphopantetheinyl transferase, to afford labeled CurB carrier proteins.

AB - A general strategy to enzymatically label acyl carrier proteins (ACPs) of polyketide synthases has been developed. Incorporation of a chloromethyl ketone or vinyl ketone moiety into polyketide chain elongation intermediate mimics allows for the synthesis of CoA adducts. These CoA adducts undergo enzymatic reaction with Sfp, a phosphopantetheinyl transferase, to afford labeled CurB carrier proteins.

KW - Acyl carrier proteins

KW - Biosynthesis

KW - Labels

KW - Polyketides

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UR - https://www.scopus.com/pages/publications/77957553811#tab=citedBy

U2 - 10.1016/j.bmcl.2010.05.089

DO - 10.1016/j.bmcl.2010.05.089

M3 - Article

C2 - 20801036

AN - SCOPUS:77957553811

SN - 0960-894X

VL - 20

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 19

ER -

A general scheme for synthesis of substrate-based polyketide labels for acyl carrier proteins

Abstract

Bibliographical note

Keywords

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