A stereochemical investigation of the cyclisation of D-glucose-6[(R)-16O,17O,18O]phosphate and adenosine-5′[(R)-16O,17O,18O]phosphate

Richard L. Jarvest, Gordon Lowe, Barry V. L. Potter

Research output: Contribution to journalArticle

Abstract

D-Glucose-6[(R)-16O,17O,18O] phosphate and adenosine-5′[(R)-16O,17O,18O] phosphate were synthesised and converted (by treatment with diphenyl phosphorochloridate, followed by potassium t-butoxide) into the cyclic 4,6-phosphate and 3′5′-phosphate diesters respectively with retention of configuration at phosphorus; the absolute configuration of D-glucose-6[16O,17O,18O]phosphate and adenosine-5′[16O,17O,18O]phosphate of unknown chirality at phosphorus can now be determined by 31P n.m.r. spectroscopy

Original languageEnglish
Pages (from-to)1142-1145
JournalJournal of the Chemical Society, Chemical Communications
Volume1980
Issue number23
DOIs
Publication statusPublished - 1980

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Cyclization
Adenosine Monophosphate
Phosphates
Glucose
Phosphorus
Spectrum Analysis
Potassium

Cite this

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title = "A stereochemical investigation of the cyclisation of D-glucose-6[(R)-16O,17O,18O]phosphate and adenosine-5′[(R)-16O,17O,18O]phosphate",
abstract = "D-Glucose-6[(R)-16O,17O,18O] phosphate and adenosine-5′[(R)-16O,17O,18O] phosphate were synthesised and converted (by treatment with diphenyl phosphorochloridate, followed by potassium t-butoxide) into the cyclic 4,6-phosphate and 3′5′-phosphate diesters respectively with retention of configuration at phosphorus; the absolute configuration of D-glucose-6[16O,17O,18O]phosphate and adenosine-5′[16O,17O,18O]phosphate of unknown chirality at phosphorus can now be determined by 31P n.m.r. spectroscopy",
author = "Jarvest, {Richard L.} and Gordon Lowe and Potter, {Barry V. L.}",
year = "1980",
doi = "10.1039/C39800001142",
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journal = "Journal of the Chemical Society, Chemical Communications",
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TY - JOUR

T1 - A stereochemical investigation of the cyclisation of D-glucose-6[(R)-16O,17O,18O]phosphate and adenosine-5′[(R)-16O,17O,18O]phosphate

AU - Jarvest, Richard L.

AU - Lowe, Gordon

AU - Potter, Barry V. L.

PY - 1980

Y1 - 1980

N2 - D-Glucose-6[(R)-16O,17O,18O] phosphate and adenosine-5′[(R)-16O,17O,18O] phosphate were synthesised and converted (by treatment with diphenyl phosphorochloridate, followed by potassium t-butoxide) into the cyclic 4,6-phosphate and 3′5′-phosphate diesters respectively with retention of configuration at phosphorus; the absolute configuration of D-glucose-6[16O,17O,18O]phosphate and adenosine-5′[16O,17O,18O]phosphate of unknown chirality at phosphorus can now be determined by 31P n.m.r. spectroscopy

AB - D-Glucose-6[(R)-16O,17O,18O] phosphate and adenosine-5′[(R)-16O,17O,18O] phosphate were synthesised and converted (by treatment with diphenyl phosphorochloridate, followed by potassium t-butoxide) into the cyclic 4,6-phosphate and 3′5′-phosphate diesters respectively with retention of configuration at phosphorus; the absolute configuration of D-glucose-6[16O,17O,18O]phosphate and adenosine-5′[16O,17O,18O]phosphate of unknown chirality at phosphorus can now be determined by 31P n.m.r. spectroscopy

UR - http://dx.doi.org/10.1039/C39800001142

U2 - 10.1039/C39800001142

DO - 10.1039/C39800001142

M3 - Article

VL - 1980

SP - 1142

EP - 1145

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

SN - 0022-4936

IS - 23

ER -