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

75 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
Publication status	Published - Feb 24 1997

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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Furneaux, R. H., Limberg, G., Tyler, P. C., & Schramm, V. L. (1997). Synthesis of transition state inhibitors for N-riboside hydrolases and transferases. Tetrahedron, 53(8), 2915-2930. https://doi.org/10.1016/S0040-4020(96)01172-6

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AU - Furneaux, Richard H.

AU - Limberg, Gerrit

AU - Tyler, Peter C.

AU - Schramm, Vern L.

PY - 1997/2/24

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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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10.1016/S0040-4020(96)01172-6