TY - JOUR
T1 - Stereochemistry of hydrogen introduction at C-25 in ergosterol synthesized by the mevalonate-independent pathway
AU - Zhou, Wen Xu
AU - Nes, W. David
PY - 2000/4/15
Y1 - 2000/4/15
N2 - Feeding of [1-13C]glucose to Prototheca wickerhamii followed by 13C NMR analysis of the resulting 13C-labeled ergosterol demonstrated this yeast-like alga operates the mevalonate-independent pathway. Based on the 13C NMR signal assignment of [2,6,11,12,16,18,19, 21,23,27-13C10] ergosterol synthesized from [1-13C]glucose indicated the pro-Z methyl group of cycloartenol is derived from C-5 of IPP and that protonation at C-25 of the Δ(25(27))-sterol intermediate takes place from the Si-face of Δ25 to form the isopropyl pro-R methyl group. (C) 2000 Elsevier Science Ltd.
AB - Feeding of [1-13C]glucose to Prototheca wickerhamii followed by 13C NMR analysis of the resulting 13C-labeled ergosterol demonstrated this yeast-like alga operates the mevalonate-independent pathway. Based on the 13C NMR signal assignment of [2,6,11,12,16,18,19, 21,23,27-13C10] ergosterol synthesized from [1-13C]glucose indicated the pro-Z methyl group of cycloartenol is derived from C-5 of IPP and that protonation at C-25 of the Δ(25(27))-sterol intermediate takes place from the Si-face of Δ25 to form the isopropyl pro-R methyl group. (C) 2000 Elsevier Science Ltd.
KW - Biosynthesis
KW - Ergosterol
KW - Non-mevalonate pathway
KW - Prototheca wickerhamii
UR - http://www.scopus.com/inward/record.url?scp=0034656098&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)00265-3
DO - 10.1016/S0040-4039(00)00265-3
M3 - Article
AN - SCOPUS:0034656098
VL - 41
SP - 2791
EP - 2795
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 16
ER -