Variable stereochemistry in highly branched isoprenoids from diatoms.

Abstract:

:C(25) highly branched isoprenoid (HBI) alkenes are ubiquitous lipids found in geochemical samples around the globe. The origins of these widespread geochemicals are believed to be restricted to a limited number of diatoms, including Haslea ostrearia (and related species), Rhizosolenia setigera, and Pleurosigma intermedium. The unsaturation of the HBI alkenes ranges from 2-6 in different species and cultures. The number of stereogenic centres is usually limited to two in the HBI alkenes due to double bond positions. The relative and/or absolute configurations for these have been determined for a range of HBI alkenes produced from different diatoms cultured under a number of growth conditions. These determinations have involved a combined spectroscopic and chromatographic analysis using NMR spectroscopy and chiral gas chromatography, respectively. HBIs isolated from Haslea spp. belong to a specific structural type which exhibit configurational diastereoisomerism, while those isolated from P. intermedium and R. setigera represent a different structural type and usually exist as mixtures of geometric isomers only. HBIs are reported from a new species of diatom whose stereochemical properties lie between those found for Haslea spp. and P. intermedium.

journal_name

Chirality

journal_title

Chirality

authors

Belt ST,Allard WG,Johns L,König WA,Massé G,Robert JM,Rowland S

doi

10.1002/chir.1053

subject

Has Abstract

pub_date

2001-08-01 00:00:00

pages

415-9

issue

8

eissn

0899-0042

issn

1520-636X

pii

10.1002/chir.1053

journal_volume

13

pub_type

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