Journal of Lipid Research, Vol 23, 352-356, Copyright © 1982 by Lipid Research, Inc.
Biotransformation of 16 alpha-hydroxyprogesterone by Eubacterium sp. 144: non-enzymatic addition of L-cysteine to delta 16-progesterone
TL Glass, J Winter, VD Bokkenheuser and PB Hylemon
Eubacterium sp. 144 dehydroxylated 16 alpha-hydroxy-progesterone; however,
the expected intermediate, delta 16-progesterone, did not accumulate to
significant concentrations in the culture medium. Moreover, the final end
product of this biotransformation, 17 alpha- progesterone, was produced at
a very slow rate. It was discovered that, under our culture conditions,
delta 16-progesterone reacted chemically with L-cysteine to form a highly
water-soluble derivative. The ability of delta 16-progesterone to react
with L-cysteine in culture media was considerably reduced when L-cysteine
was autoclaved in the presence of complex medium components. delta
16-Progesterone also reacted chemically with D-cysteine, L-homocysteine,
glutathione, and 2- mercaptoethylamine. The reaction was favored by
alkaline pH (greater than or equal to pH 8.0) and required both an
unhindered thiol group and a proximal amino group on the mercapto compound.
Chromatography of the putative delta 16-progesterone L-[U-14C]-cysteine
reaction product by HPLC showed a single UV-absorbing, radioactive peak (RT
4.31 min).
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