The oxetane conformational lock of paclitaxel: structural analysis of D-secopaclitaxel

T C Boge; M Hepperle; D G Vander Velde; C W Gunn; G L Grunewald; G I Georg

doi:10.1016/s0960-894x(99)00521-1

The oxetane conformational lock of paclitaxel: structural analysis of D-secopaclitaxel

Bioorg Med Chem Lett. 1999 Oct 18;9(20):3041-6. doi: 10.1016/s0960-894x(99)00521-1.

Authors

T C Boge¹, M Hepperle, D G Vander Velde, C W Gunn, G L Grunewald, G I Georg

Affiliation

¹ Department of Medicinal Chemistry, University of Kansas, Lawrence 66045, USA.

PMID: 10571172
DOI: 10.1016/s0960-894x(99)00521-1

Abstract

Analysis of the 1H NMR data of paclitaxel in comparison with its oxetane ring-opened analogue D-secopaclitaxel suggests that the oxetane moiety (D-ring) of paclitaxel serves as a conformational lock for the diterpene moiety and the C13 side chain.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry*
Magnetic Resonance Spectroscopy
Molecular Conformation
Paclitaxel / chemistry*
Stereoisomerism

Substances

Antineoplastic Agents, Phytogenic
Paclitaxel