SYNTHESIS OF (-(1S)-1-PYROPHOSPHORYL-(2R, IHYDROXY-(4S)-4-(PHOSPHORYLOXYMETHYL)CYCLOPENTANE, A STABLE, OPTICALLY-ACTIVE CARBOCYCLIC ANALOG OF 5-PHOSPHORIBOSYL-1-PYROPHOSPHATE (PRPP)())

Authors
PARRY RJ BURNS MR JIRALERSPONG S ALEMANY L
Citation
Rj. Parry et al., SYNTHESIS OF (-(1S)-1-PYROPHOSPHORYL-(2R, IHYDROXY-(4S)-4-(PHOSPHORYLOXYMETHYL)CYCLOPENTANE, A STABLE, OPTICALLY-ACTIVE CARBOCYCLIC ANALOG OF 5-PHOSPHORIBOSYL-1-PYROPHOSPHATE (PRPP)()), Tetrahedron, 53(21), 1997, pp. 7077-7088
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
21
Year of publication
1997
Pages
7077 - 7088
Database
ISI
SICI code
0040-4020(1997)53:21<7077:SO(I>2.0.ZU;2-H
Abstract
A total synthesis of the cyclopentyl analog of the important biochemic al intermediate 5-phosphoribosyl-1-pyrophosphate (PRPP) is reported. T he synthesis proceeds from the benzylidene acetal of D-ribonolactone t o the correct enantiomeric form of the cyclopentyl PRPP analog in ca. 4% overall yield. Because of the low reactivity of the carbocyclic ana log compared to PRPP, the compound should be a highly useful tool for mechanistic and crystallographic investigations of the phosphoribosylt ransferases, a family of enzymes that utilizes PRPP as a substrate. (C ) 1997 Elsevier Science Ltd.