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A protecting group-free synthesis of deazathiamine: A step toward inhibitor design

The discovery of 3-deazathiamine diphosphate (deazaThDP) as a potent inhibitor analog of the cofactor thiamine diphosphate (ThDP) has highlighted the need for an efficient and scalable synthesis of deazaThDP. Such a method would facilitate development of analogs with the ability to inhibit individua... Full description

Journal Title: Bioorganic & Medicinal Chemistry Letters 2010, Vol.20(22), pp.6472-6474
Main Author: Zhao, Hong
Other Authors: de Carvalho, Luiz Pedro S , Nathan, Carl , Ouerfelli, Ouathek
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0960-894X ; E-ISSN: 1464-3405 ; DOI: 10.1016/j.bmcl.2010.09.053
Link: https://www.sciencedirect.com/science/article/pii/S0960894X10013545
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recordid: elsevier_sdoi_10_1016_j_bmcl_2010_09_053
title: A protecting group-free synthesis of deazathiamine: A step toward inhibitor design
format: Article
creator:
  • Zhao, Hong
  • de Carvalho, Luiz Pedro S
  • Nathan, Carl
  • Ouerfelli, Ouathek
subjects:
  • Deazathiamine
  • 3-Deazathiaminediphosphate
  • 3-Deazathiamine
  • 3-Deazathiamine Synthesis
  • 2,3,5-Tribromo-3-Methylthiophene
  • Medicine
  • Chemistry
  • Anatomy & Physiology
ispartof: Bioorganic & Medicinal Chemistry Letters, 2010, Vol.20(22), pp.6472-6474
description: The discovery of 3-deazathiamine diphosphate (deazaThDP) as a potent inhibitor analog of the cofactor thiamine diphosphate (ThDP) has highlighted the need for an efficient and scalable synthesis of deazaThDP. Such a method would facilitate development of analogs with the ability to inhibit individual ThDP-dependent enzymes selectively. Toward the goal of developing selective inhibitors of the mycobacterial enzyme 2-hydroxy-3-oxoadipate synthase (HOAS), we report an improved synthesis of deazaThDP without use of protecting groups. Tribromo-3-methylthiophene served as a versatile starting material whose selective functionalization permitted access to deazaThDP in five steps, with potential to make other analogs accessible in substantial amounts.
language: eng
source:
identifier: ISSN: 0960-894X ; E-ISSN: 1464-3405 ; DOI: 10.1016/j.bmcl.2010.09.053
fulltext: fulltext
issn:
  • 0960-894X
  • 0960894X
  • 1464-3405
  • 14643405
url: Link


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titleA protecting group-free synthesis of deazathiamine: A step toward inhibitor design
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descriptionThe discovery of 3-deazathiamine diphosphate (deazaThDP) as a potent inhibitor analog of the cofactor thiamine diphosphate (ThDP) has highlighted the need for an efficient and scalable synthesis of deazaThDP. Such a method would facilitate development of analogs with the ability to inhibit individual ThDP-dependent enzymes selectively. Toward the goal of developing selective inhibitors of the mycobacterial enzyme 2-hydroxy-3-oxoadipate synthase (HOAS), we report an improved synthesis of deazaThDP without use of protecting groups. Tribromo-3-methylthiophene served as a versatile starting material whose selective functionalization permitted access to deazaThDP in five steps, with potential to make other analogs accessible in substantial amounts.
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The discovery of 3-deazathiamine diphosphate (deazaThDP) as a potent inhibitor analog of the cofactor thiamine diphosphate (ThDP) has highlighted the need for an efficient and scalable synthesis of deazaThDP. Such a method would facilitate development of analogs with the ability to inhibit individual ThDP-dependent enzymes selectively. Toward the goal of developing selective inhibitors of the mycobacterial enzyme 2-hydroxy-3-oxoadipate synthase (HOAS), we report an improved synthesis of deazaThDP without use of protecting groups. Tribromo-3-methylthiophene served as a versatile starting material whose selective functionalization permitted access to deazaThDP in five steps, with potential to make other analogs accessible in substantial amounts.

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The discovery of 3-deazathiamine diphosphate (deazaThDP) as a potent inhibitor analog of the cofactor thiamine diphosphate (ThDP) has highlighted the need for an efficient and scalable synthesis of deazaThDP. Such a method would facilitate development of analogs with the ability to inhibit individual ThDP-dependent enzymes selectively. Toward the goal of developing selective inhibitors of the mycobacterial enzyme 2-hydroxy-3-oxoadipate synthase (HOAS), we report an improved synthesis of deazaThDP without use of protecting groups. Tribromo-3-methylthiophene served as a versatile starting material whose selective functionalization permitted access to deazaThDP in five steps, with potential to make other analogs accessible in substantial amounts.

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date2010-11-15