Synthesis of transition state inhibitors for N-riboside hydrolases and transferases

Richard H. Furneaux; Gerrit Limberg; Peter C. Tyler; Vern L. Schramm

doi:10.1016/S0040-4020(96)01172-6

Synthesis of transition state inhibitors for N-riboside hydrolases and transferases

Richard H. Furneaux, Gerrit Limberg, Peter C. Tyler, Vern L. Schramm

Biochemistry

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

77 Scopus citations

Abstract

A number of 1,4-dideoxy-1,4-imino-1-(S)-(substituted phenyl)-D-ribitols bearing aromatic OH, NH₂, NO₂, CO₂H and halogeno moieties, and a 3-pyridyl analogue have been synthesized. The key step is die condensation of aryllithium or aryl Grignard reagents with the imine 3; derived from the protected 1,4-dideoxy-1,4-imino-D-ribitol 4.

Original language	English (US)
Pages (from-to)	2915-2930
Number of pages	16
Journal	Tetrahedron
Volume	53
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4020(96)01172-6
State	Published - Feb 24 1997

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "A number of 1,4-dideoxy-1,4-imino-1-(S)-(substituted phenyl)-D-ribitols bearing aromatic OH, NH2, NO2, CO2H and halogeno moieties, and a 3-pyridyl analogue have been synthesized. The key step is die condensation of aryllithium or aryl Grignard reagents with the imine 3; derived from the protected 1,4-dideoxy-1,4-imino-D-ribitol 4.",

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T1 - Synthesis of transition state inhibitors for N-riboside hydrolases and transferases

AU - Furneaux, Richard H.

AU - Limberg, Gerrit

AU - Tyler, Peter C.

AU - Schramm, Vern L.

PY - 1997/2/24

Y1 - 1997/2/24

N2 - A number of 1,4-dideoxy-1,4-imino-1-(S)-(substituted phenyl)-D-ribitols bearing aromatic OH, NH2, NO2, CO2H and halogeno moieties, and a 3-pyridyl analogue have been synthesized. The key step is die condensation of aryllithium or aryl Grignard reagents with the imine 3; derived from the protected 1,4-dideoxy-1,4-imino-D-ribitol 4.

AB - A number of 1,4-dideoxy-1,4-imino-1-(S)-(substituted phenyl)-D-ribitols bearing aromatic OH, NH2, NO2, CO2H and halogeno moieties, and a 3-pyridyl analogue have been synthesized. The key step is die condensation of aryllithium or aryl Grignard reagents with the imine 3; derived from the protected 1,4-dideoxy-1,4-imino-D-ribitol 4.

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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