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

79 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

Access to Document

10.1016/S0040-4020(96)01172-6

Cite this

@article{1c1fdad5e622461097a0f0174b7a7d0d,

title = "Synthesis of transition state inhibitors for N-riboside hydrolases and transferases",

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.",

author = "Furneaux, \{Richard H.\} and Gerrit Limberg and Tyler, \{Peter C.\} and Schramm, \{Vern L.\}",

note = "Funding Information: This work was supported by research grants AI 34342 and GM 41916 from the National Institute of Health, USA and by the New Zealand Foundation for Research Science and Technology, contract C08301. Dr Herbert Wong is thanked for a superb n.mr. service.",

year = "1997",

month = feb,

day = "24",

doi = "10.1016/S0040-4020(96)01172-6",

language = "English (US)",

volume = "53",

pages = "2915--2930",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "8",

}

TY - JOUR

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.

N1 - Funding Information: This work was supported by research grants AI 34342 and GM 41916 from the National Institute of Health, USA and by the New Zealand Foundation for Research Science and Technology, contract C08301. Dr Herbert Wong is thanked for a superb n.mr. service.

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.

UR - https://www.scopus.com/pages/publications/0031584878

UR - https://www.scopus.com/pages/publications/0031584878#tab=citedBy

U2 - 10.1016/S0040-4020(96)01172-6

DO - 10.1016/S0040-4020(96)01172-6

M3 - Article

AN - SCOPUS:0031584878

SN - 0040-4020

VL - 53

SP - 2915

EP - 2930

JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this