d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses

Izabela Fokt; Slawomir Szymanski; Stanislaw Skora; Marcin Cybulski; Timothy Madden; Waldemar Priebe

doi:10.1016/j.carres.2009.06.016

d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses

Izabela Fokt, Slawomir Szymanski, Stanislaw Skora, Marcin Cybulski, Timothy Madden, Waldemar Priebe

Experimental Therapeutics

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

22 Scopus citations

Abstract

Modified d-glucose and d-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives of d-glucose and d-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-d-glucal.

Original language	English (US)
Pages (from-to)	1464-1473
Number of pages	10
Journal	Carbohydrate Research
Volume	344
Issue number	12
DOIs	https://doi.org/10.1016/j.carres.2009.06.016
State	Published - Aug 17 2009

Keywords

2-Deoxy-2-halo-d-glucose
2-Deoxy-2-halo-d-mannose
Inhibitors of glycolysis
Synthesis

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

MD Anderson CCSG core facilities

NMR Facility

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10.1016/j.carres.2009.06.016

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title = "d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses",

abstract = "Modified d-glucose and d-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives of d-glucose and d-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-d-glucal.",

keywords = "2-Deoxy-2-halo-d-glucose, 2-Deoxy-2-halo-d-mannose, Inhibitors of glycolysis, Synthesis",

author = "Izabela Fokt and Slawomir Szymanski and Stanislaw Skora and Marcin Cybulski and Timothy Madden and Waldemar Priebe",

note = "Funding Information: This work was supported in part by NCI SPORE in a Pancreatic Cancer P20 CA101936 grant (WP) and The Morton and Angela Topfer Pancreatic Cancer Research Fund (WP). We also acknowledge the NCI Cancer Center Support Grant CA016672 for the support of NMR facility at UT M. D. Anderson Cancer Center.",

year = "2009",

month = aug,

day = "17",

doi = "10.1016/j.carres.2009.06.016",

language = "English (US)",

volume = "344",

pages = "1464--1473",

journal = "Carbohydrate Research",

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T1 - d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses

AU - Fokt, Izabela

AU - Szymanski, Slawomir

AU - Skora, Stanislaw

AU - Cybulski, Marcin

AU - Madden, Timothy

AU - Priebe, Waldemar

N1 - Funding Information: This work was supported in part by NCI SPORE in a Pancreatic Cancer P20 CA101936 grant (WP) and The Morton and Angela Topfer Pancreatic Cancer Research Fund (WP). We also acknowledge the NCI Cancer Center Support Grant CA016672 for the support of NMR facility at UT M. D. Anderson Cancer Center.

PY - 2009/8/17

Y1 - 2009/8/17

N2 - Modified d-glucose and d-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives of d-glucose and d-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-d-glucal.

AB - Modified d-glucose and d-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives of d-glucose and d-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-d-glucal.

KW - 2-Deoxy-2-halo-d-glucose

KW - 2-Deoxy-2-halo-d-mannose

KW - Inhibitors of glycolysis

KW - Synthesis

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AN - SCOPUS:68249111862

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SP - 1464

EP - 1473

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 12

ER -

d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses

Abstract

Keywords

ASJC Scopus subject areas

MD Anderson CCSG core facilities

Access to Document

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