Sterol synthesis. Chemical synthesis, structure determination and metabolism of 14α-methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol

Thomas E. Spike; Joseph A. Martin; Steven Huntoon; Andrew HC Wang; Furn F. Knapp; George J. Schroepfer

doi:10.1016/0009-3084(78)90053-1

Sterol synthesis. Chemical synthesis, structure determination and metabolism of 14α-methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol

Thomas E. Spike
, Joseph A. Martin
, Steven Huntoon
, Andrew HC Wang
, Furn F. Knapp
, George J. Schroepfer

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

14α-Methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol have been prepared by chemical synthesis. Unequivocal establishment of these structures was based upon x-ray crratallographic analysis of 3β-p-bromobenzoyloxy-14α-methyl-5α-cholest-7-en-15 β-ol and was supported by other spectroscopic data. Spectroscopic data were presented for the following compounds prepared in this study: 3β-benzoyloxy-5α-cholest-8(14)-en-15-one, 3β-benzoyloxy-14α-methyl-5α-cholest-7-en-15-one, 3β-benzoyloxy-14α-methyl-5α-cholest-7-en-15β-ol, 14α-methyl-5α-cholest-7-en-3β, 15β 15β-diol, 14α-methyl-5α-cholest-7-en-3β,15α-diol, 3β, 15α-bis-benzoyloxy-14α-methyl-5α-cholest-7-ene, 3β-bromobenzoyloxy-14α-methyl-5α-cholest-7-en-15β- ol and 3β, 15β-bis-p-bromobenzoyloxy-14α-methyl-15α-cholest-7-ene. Studies of the metabolism of [16-³H]-14α-methyl-5α-cholest-7-en-3β ,15β-diol [16-³H]-14α-methyl-5α-cholest-7-en-3β, 15α-diol in liver homogenates of female rats indicated that only the 3β,15β-diol was convertible to cholesterol.

Original language	English
Pages (from-to)	31-58
Number of pages	28
Journal	Chemistry and Physics of Lipids
Volume	21
Issue number	1-2
DOIs	https://doi.org/10.1016/0009-3084(78)90053-1
Publication status	Published - Apr 1978
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Organic Chemistry
Cell Biology

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10.1016/0009-3084(78)90053-1

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Sterol synthesis. Chemical synthesis, structure determination and metabolism of 14α-methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol. / Spike, Thomas E.; Martin, Joseph A.; Huntoon, Steven et al.
In: Chemistry and Physics of Lipids, Vol. 21, No. 1-2, 04.1978, p. 31-58.

Research output: Contribution to journal › Article › peer-review

@article{cf0b237a7b80438684ae24167ccdbc21,

title = "Sterol synthesis. Chemical synthesis, structure determination and metabolism of 14α-methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol",

abstract = "14α-Methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol have been prepared by chemical synthesis. Unequivocal establishment of these structures was based upon x-ray crratallographic analysis of 3β-p-bromobenzoyloxy-14α-methyl-5α-cholest-7-en-15 β-ol and was supported by other spectroscopic data. Spectroscopic data were presented for the following compounds prepared in this study: 3β-benzoyloxy-5α-cholest-8(14)-en-15-one, 3β-benzoyloxy-14α-methyl-5α-cholest-7-en-15-one, 3β-benzoyloxy-14α-methyl-5α-cholest-7-en-15β-ol, 14α-methyl-5α-cholest-7-en-3β, 15β 15β-diol, 14α-methyl-5α-cholest-7-en-3β,15α-diol, 3β, 15α-bis-benzoyloxy-14α-methyl-5α-cholest-7-ene, 3β-bromobenzoyloxy-14α-methyl-5α-cholest-7-en-15β- ol and 3β, 15β-bis-p-bromobenzoyloxy-14α-methyl-15α-cholest-7-ene. Studies of the metabolism of [16-3H]-14α-methyl-5α-cholest-7-en-3β ,15β-diol [16-3H]-14α-methyl-5α-cholest-7-en-3β, 15α-diol in liver homogenates of female rats indicated that only the 3β,15β-diol was convertible to cholesterol.",

author = "Spike, \{Thomas E.\} and Martin, \{Joseph A.\} and Steven Huntoon and Wang, \{Andrew HC\} and Knapp, \{Furn F.\} and Schroepfer, \{George J.\}",

note = "Funding Information: This work was supported in part by grants from the National Institutes of ttea!th (HL.O9501 and HL-15376), the Robert A. Welch Foundation \textasciitilde{}d the Illinois Heart Association. T.E.S. w\textasciitilde{} supported by a National Institutes of Health Predoctoral Traineeship. We {"},dso wish to acknowledge the advice and encouragement of Professor !.C. Paul in the X-ray crystallographic studies.",

year = "1978",

month = apr,

doi = "10.1016/0009-3084(78)90053-1",

language = "English",

volume = "21",

pages = "31--58",

journal = "Chemistry and Physics of Lipids",

issn = "0009-3084",

publisher = "Elsevier Ireland Ltd",

number = "1-2",

}

TY - JOUR

T1 - Sterol synthesis. Chemical synthesis, structure determination and metabolism of 14α-methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol

AU - Spike, Thomas E.

AU - Martin, Joseph A.

AU - Huntoon, Steven

AU - Wang, Andrew HC

AU - Knapp, Furn F.

AU - Schroepfer, George J.

N1 - Funding Information: This work was supported in part by grants from the National Institutes of ttea!th (HL.O9501 and HL-15376), the Robert A. Welch Foundation ~d the Illinois Heart Association. T.E.S. w~ supported by a National Institutes of Health Predoctoral Traineeship. We ",dso wish to acknowledge the advice and encouragement of Professor !.C. Paul in the X-ray crystallographic studies.

PY - 1978/4

Y1 - 1978/4

N2 - 14α-Methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol have been prepared by chemical synthesis. Unequivocal establishment of these structures was based upon x-ray crratallographic analysis of 3β-p-bromobenzoyloxy-14α-methyl-5α-cholest-7-en-15 β-ol and was supported by other spectroscopic data. Spectroscopic data were presented for the following compounds prepared in this study: 3β-benzoyloxy-5α-cholest-8(14)-en-15-one, 3β-benzoyloxy-14α-methyl-5α-cholest-7-en-15-one, 3β-benzoyloxy-14α-methyl-5α-cholest-7-en-15β-ol, 14α-methyl-5α-cholest-7-en-3β, 15β 15β-diol, 14α-methyl-5α-cholest-7-en-3β,15α-diol, 3β, 15α-bis-benzoyloxy-14α-methyl-5α-cholest-7-ene, 3β-bromobenzoyloxy-14α-methyl-5α-cholest-7-en-15β- ol and 3β, 15β-bis-p-bromobenzoyloxy-14α-methyl-15α-cholest-7-ene. Studies of the metabolism of [16-3H]-14α-methyl-5α-cholest-7-en-3β ,15β-diol [16-3H]-14α-methyl-5α-cholest-7-en-3β, 15α-diol in liver homogenates of female rats indicated that only the 3β,15β-diol was convertible to cholesterol.

AB - 14α-Methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol have been prepared by chemical synthesis. Unequivocal establishment of these structures was based upon x-ray crratallographic analysis of 3β-p-bromobenzoyloxy-14α-methyl-5α-cholest-7-en-15 β-ol and was supported by other spectroscopic data. Spectroscopic data were presented for the following compounds prepared in this study: 3β-benzoyloxy-5α-cholest-8(14)-en-15-one, 3β-benzoyloxy-14α-methyl-5α-cholest-7-en-15-one, 3β-benzoyloxy-14α-methyl-5α-cholest-7-en-15β-ol, 14α-methyl-5α-cholest-7-en-3β, 15β 15β-diol, 14α-methyl-5α-cholest-7-en-3β,15α-diol, 3β, 15α-bis-benzoyloxy-14α-methyl-5α-cholest-7-ene, 3β-bromobenzoyloxy-14α-methyl-5α-cholest-7-en-15β- ol and 3β, 15β-bis-p-bromobenzoyloxy-14α-methyl-15α-cholest-7-ene. Studies of the metabolism of [16-3H]-14α-methyl-5α-cholest-7-en-3β ,15β-diol [16-3H]-14α-methyl-5α-cholest-7-en-3β, 15α-diol in liver homogenates of female rats indicated that only the 3β,15β-diol was convertible to cholesterol.

UR - https://www.scopus.com/pages/publications/0017953494

UR - https://www.scopus.com/pages/publications/0017953494#tab=citedBy

U2 - 10.1016/0009-3084(78)90053-1

DO - 10.1016/0009-3084(78)90053-1

M3 - Article

C2 - 668029

AN - SCOPUS:0017953494

SN - 0009-3084

VL - 21

SP - 31

EP - 58

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

IS - 1-2

ER -

Sterol synthesis. Chemical synthesis, structure determination and metabolism of 14α-methyl-5α-cholest-7-en-3β, 15β-diol and 14α-methyl-5α-cholest-7-en-3β, 15α-diol

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