The porphynoid pigments of the Caribbean tunicate Trididemnum solidum

Tunichlorin, a nickel chlorin isolated from the Caribbean tunicate Trididemnum solidum, has been identified as nickel (II) 2-devinyl-2-hydroxymethylpyropheophorbide a by chemical and spectroscopic methods. A partial synthesis of dimethyl tunichlorin from chlorophyll a (7 steps, 5% overall yield) has also confirmed the proposed structure. In the living tunicate, tunichlorin appears to exist primarily as a series of C-14 to C-18 ester homologues (principally tunichlorin-COO-(C$\sb3$H$\sb4$O)-(CH$\sb2$)$\sb{14}$CH$\sb3$). Preliminary studies suggest that tunichlorin esters are biosynthesized by the tunicate from alga-produced chlorophyll a. Although the biological function of tunichlorin esters remains unclear, analogy to related compounds suggests that they may be enzyme cofactors involved in reductive processes.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Bible, Keith Christopher

Contributors dc:contributor

• Rinehart, Kenneth L., Jr.

• Chemistry, Biochemistry
• Chemistry, Organic

Statement dc:rights

• Copyright 1989 Bible, Keith Christopher

Language dc:language

eng

Identifier

AAI9010806
(UMI)AAI9010806

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/20082