Investigation of the importance of the C-2 and C-13 oxygen functions in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145.
Incubation of 2alpha,13(R)-dihydroxystemodane (3) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(R)-trihydroxystemodane (11) while biotransformation of 13(R)-hydroxystemodan-2-one (5) yielded 6alpha,13(R)-dihydroxystemodan-2-one (12) and 7beta,13(R)-dihydroxystemodan-2-one (13). Bioconversion of 2beta,13(R)-dihydroxystemodane (7) with Rhizopus afforded 2beta,7,13(R)-trihydroxystemodane (14). The results complement data from our previous work and provide more information about the effect of functional groups of stemodane substrates on the site of hydroxylation.
Martin
Glenroy D A
GD
Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica.
Reynolds
William F
WF
Reese
Paul B
PB
D001711:Biotransformation; D002384:Catalysis; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D006900:Hydroxylation; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D012233:Rhizopus / Q000378:metabolism*; D013237:Stereoisomerism
D004224:Diterpenes; C074341:stemodin; D010100:Oxygen