Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer

S D  Wang; S J  McClue; J R  Ferguson; J D  Hull; S  Stokes; S  Parsons; R  Westwood; P M  Fischer

Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer

S D Wang, S J McClue, J R Ferguson, J D Hull, S Stokes, S Parsons, R Westwood, P M Fischer

School of Chemistry

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

Abstract

The cyclin-dependent kinase inhibitor (R)-2-(6-benzylamino-9-isopropyl-9H-purin-2-ylamino)butan-1-ol (roscovitine, 1a), as well as its (S)-enantiomer 1b, were synthesised. The chemical structure and absolute configuration of both enantiomers was confirmed by X-ray crystallography. Furthermore, high enantiomeric excess (>98%) was demonstrated by chiral chromatography of la and 1b, as well as NMR analysis of the diastereomeric Mosher's ester derivatives 2a and 2b. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	2891-2894
Number of pages	4
Journal	Tetrahedron: Asymmetry
Volume	12
Issue number	20
Publication status	Published - 13 Nov 2001

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title = "Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer",

abstract = "The cyclin-dependent kinase inhibitor (R)-2-(6-benzylamino-9-isopropyl-9H-purin-2-ylamino)butan-1-ol (roscovitine, 1a), as well as its (S)-enantiomer 1b, were synthesised. The chemical structure and absolute configuration of both enantiomers was confirmed by X-ray crystallography. Furthermore, high enantiomeric excess (>98\%) was demonstrated by chiral chromatography of la and 1b, as well as NMR analysis of the diastereomeric Mosher's ester derivatives 2a and 2b. (C) 2001 Elsevier Science Ltd. All rights reserved.",

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T1 - Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer

AU - Wang, S D

AU - McClue, S J

AU - Ferguson, J R

AU - Hull, J D

AU - Stokes, S

AU - Parsons, S

AU - Westwood, R

AU - Fischer, P M

PY - 2001/11/13

Y1 - 2001/11/13

N2 - The cyclin-dependent kinase inhibitor (R)-2-(6-benzylamino-9-isopropyl-9H-purin-2-ylamino)butan-1-ol (roscovitine, 1a), as well as its (S)-enantiomer 1b, were synthesised. The chemical structure and absolute configuration of both enantiomers was confirmed by X-ray crystallography. Furthermore, high enantiomeric excess (>98%) was demonstrated by chiral chromatography of la and 1b, as well as NMR analysis of the diastereomeric Mosher's ester derivatives 2a and 2b. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - The cyclin-dependent kinase inhibitor (R)-2-(6-benzylamino-9-isopropyl-9H-purin-2-ylamino)butan-1-ol (roscovitine, 1a), as well as its (S)-enantiomer 1b, were synthesised. The chemical structure and absolute configuration of both enantiomers was confirmed by X-ray crystallography. Furthermore, high enantiomeric excess (>98%) was demonstrated by chiral chromatography of la and 1b, as well as NMR analysis of the diastereomeric Mosher's ester derivatives 2a and 2b. (C) 2001 Elsevier Science Ltd. All rights reserved.

M3 - Article

SN - 0957-4166

VL - 12

SP - 2891

EP - 2894

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 20

ER -

Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer

Abstract

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