TY - JOUR
T1 - Microbial Formation of 17α‐C21 Steroids
T2 - Stereochemistry of Saturation of the Δ16‐Double Bond
AU - Björkhem, Ingemar
AU - Eriksson, Håkan
AU - Gustafsson, Jan‐Åke
PY - 1971/6
Y1 - 1971/6
N2 - After anaerobic incubation in deuterated water of 3β‐hydroxy‐5,16‐pregnadien‐20‐one with caecal contents from rats, 3β‐hydroxy‐17α‐pregn‐5‐en‐20‐one with deuterium label in ring D was isolated. Enolization of this compound with alkali yielded 3β‐hydroxy‐17β‐pregn‐5‐en‐20‐one with about 0.4 atoms of deuterim in ring D. Incubation of this compound with rat liver microsomes fortified with NADPH yielded 3β,16α‐dihydroxy‐17β‐pregn‐5‐en‐20‐one devoid of deuterium in ring D. The results show that the saturation of the Δ16‐double bond, catalyzed by intestinal microorganisms, involves a trans addition of hydrogen to the 16α‐ and 17β‐positions.
AB - After anaerobic incubation in deuterated water of 3β‐hydroxy‐5,16‐pregnadien‐20‐one with caecal contents from rats, 3β‐hydroxy‐17α‐pregn‐5‐en‐20‐one with deuterium label in ring D was isolated. Enolization of this compound with alkali yielded 3β‐hydroxy‐17β‐pregn‐5‐en‐20‐one with about 0.4 atoms of deuterim in ring D. Incubation of this compound with rat liver microsomes fortified with NADPH yielded 3β,16α‐dihydroxy‐17β‐pregn‐5‐en‐20‐one devoid of deuterium in ring D. The results show that the saturation of the Δ16‐double bond, catalyzed by intestinal microorganisms, involves a trans addition of hydrogen to the 16α‐ and 17β‐positions.
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U2 - 10.1111/j.1432-1033.1971.tb01399.x
DO - 10.1111/j.1432-1033.1971.tb01399.x
M3 - Article
C2 - 4397228
AN - SCOPUS:0015219736
SN - 0014-2956
VL - 20
SP - 340
EP - 343
JO - European Journal of Biochemistry
JF - European Journal of Biochemistry
IS - 3
ER -