Stereochemical studies of acyclic isoprenoid compounds: IV. Microbial oxidation of 2,6,10,14-tetramethylpentadecane(pristane)

• Published in: Biochimica et biophysica acta. Lipids and lipid metabolism Vol. 360; no. 2; pp. 166 - 173
• Main Authors: Cox, R.E., Maxwell, J.R., Ackman, R.G., Hooper, S.N.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 22.08.1974
• ISSN: 0005-2760; 1879-145X
• DOI: 10.1016/0005-2760(74)90166-0

Mycobacterium fortuitum utilises 2,6,10,14-tetramethylpentadecane (pristane) as the sole carbon source. Products isolated from the bacterial lipids included 2,6,10,14-tetramethylpentadecan-1-o1, 2,6,10,14-tetramethylpentadecanoic acid and 4,8,12-trimethyltridecanoic acid. The isolation of only the 2(RS),6(S),10(S) isomers of the C 19 alcohol and acid respectively, and of the 4(S),8(S) isomer of the C 16, acid, from oxidation of the 6(R),10(S) isomer of pristane, indicate attack at only one terminus of this substrate. When a mixture of the 6(R),10(S); 6(R),10(R); and 6(S),10(S) isomers (2:1:1) of pristane was utilised, the 6(R),10(S) isomer was preferentially oxidised.