PHOTOCHEMICAL OXIDATION OF VINDOLINE AND 16-O-ACETYLVINDOLINE

Frank J Filippelli; S E Reeg; F Sima Sariaslani; M W Duffel; JPN Rosazza

doi:10.1111/j.1751-1097.1988.tb02819.x

Back

PHOTOCHEMICAL OXIDATION OF VINDOLINE AND 16-O-ACETYLVINDOLINE

Journal article

Peer reviewed

PHOTOCHEMICAL OXIDATION OF VINDOLINE AND 16-O-ACETYLVINDOLINE

Frank J Filippelli, S E Reeg, F Sima Sariaslani, M W Duffel and JPN Rosazza

Photochemistry and photobiology, Vol.48(3), pp.265-269

09/01/1988

DOI: 10.1111/j.1751-1097.1988.tb02819.x

PMID: 3222335

View Online

Abstract

Abstract— Photooxidation of 16‐O‐acetylvindoline in methanol using chlorpromazine‐HCl as a photosensitizing agent produces nearly quantitative yields of an iminium derivative. The 16‐O‐acetylvindol‐ine‐iminium product was characterized spectrally by proton NMR and mass spectrometry; and by chemical reduction with sodium borodeuteride. Proton NMR and mass spectral analyses of the reduced product revealed that deuterium was stereospecifically incorporated into the 3‐a‐position. The iminium product formed by photochemical oxidation is identical to that produced by copper oxidases and peroxidase. Photochemical oxidation provides direct evidence for the involvement of free radicals in Aspidosperma alkaloid transformations. Copyright © 1988, Wiley Blackwell. All rights reserved

Biophysics

Biochemistry & Molecular Biology

Life Sciences & Biomedicine

Science & Technology

Details

Title: Subtitle: PHOTOCHEMICAL OXIDATION OF VINDOLINE AND 16-O-ACETYLVINDOLINE
Creators: Frank J Filippelli
S E Reeg - University of Iowa
F Sima Sariaslani - University of Iowa
M W Duffel - University of Iowa
JPN Rosazza
Resource Type: Journal article
Publication Details: Photochemistry and photobiology, Vol.48(3), pp.265-269
Publisher: AMER SOC PHOTOBIOLOGY
DOI: 10.1111/j.1751-1097.1988.tb02819.x
PMID: 3222335
ISSN: 0031-8655
eISSN: 1751-1097
Number of pages: 5
Grant note: R01CA013786 / NATIONAL CANCER INSTITUTE; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Cancer Institute (NCI) CA13786-13 / NCI NIH HHS; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Cancer Institute (NCI)
Language: English
Date published: 09/01/1988
Academic Unit: Pharmacy; Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
Record Identifier: 9984303284802771

Metrics

7 Record Views

2 Times Cited - Web of Science