Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids

Vladimir A. Khripach; Vladimir N. Zhabinskii; Olga V. Konstantinova; Natalya B. Khripach; Alexey V. Antonchick; Andrey P. Antonchick; Bernd Schneider

doi:10.1016/j.steroids.2005.02.014

Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids

Vladimir A. Khripach^*, Vladimir N. Zhabinskii, Olga V. Konstantinova, Natalya B. Khripach, Alexey V. Antonchick, Andrey P. Antonchick, Bernd Schneider

^*Corresponding author for this work

Not published at Aalto University

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

27 Citations (Scopus)

Abstract

A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3β-hydroxy-Δ⁵- or a Δ⁴-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3β-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides to sulfones prepared from (2R)- and (2S)-3-hydroxy-2-methylpropanoates. Oxidation of intermediate 26-alcohols into the corresponding carboxylic acids ensuring preservation of stereochemistry at C-25 and functional groups in the cyclic part was achieved with sodium chlorite catalyzed by TEMPO and bleach.

Original language	English
Pages (from-to)	551-562
Number of pages	12
Journal	STEROIDS
Volume	70
Issue number	8
DOIs	https://doi.org/10.1016/j.steroids.2005.02.014
Publication status	Published - 1 Jul 2005
MoE publication type	A1 Journal article-refereed

Keywords

26-Hydroxycholesterol
Biosynthesis
Cholestenoic acids
Cholic acids

Access to Document

10.1016/j.steroids.2005.02.014

Cite this

@article{d1ff6187368a4abb8a84913268fdc899,

title = "Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids",

abstract = "A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3β-hydroxy-Δ5- or a Δ4-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3β-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides to sulfones prepared from (2R)- and (2S)-3-hydroxy-2-methylpropanoates. Oxidation of intermediate 26-alcohols into the corresponding carboxylic acids ensuring preservation of stereochemistry at C-25 and functional groups in the cyclic part was achieved with sodium chlorite catalyzed by TEMPO and bleach.",

keywords = "26-Hydroxycholesterol, Biosynthesis, Cholestenoic acids, Cholic acids",

author = "Khripach, {Vladimir A.} and Zhabinskii, {Vladimir N.} and Konstantinova, {Olga V.} and Khripach, {Natalya B.} and Antonchick, {Alexey V.} and Antonchick, {Andrey P.} and Bernd Schneider",

year = "2005",

month = jul,

day = "1",

doi = "10.1016/j.steroids.2005.02.014",

language = "English",

volume = "70",

pages = "551--562",

journal = "STEROIDS",

issn = "0039-128X",

publisher = "Elsevier",

number = "8",

}

TY - JOUR

T1 - Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids

AU - Khripach, Vladimir A.

AU - Zhabinskii, Vladimir N.

AU - Konstantinova, Olga V.

AU - Khripach, Natalya B.

AU - Antonchick, Alexey V.

AU - Antonchick, Andrey P.

AU - Schneider, Bernd

PY - 2005/7/1

Y1 - 2005/7/1

N2 - A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3β-hydroxy-Δ5- or a Δ4-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3β-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides to sulfones prepared from (2R)- and (2S)-3-hydroxy-2-methylpropanoates. Oxidation of intermediate 26-alcohols into the corresponding carboxylic acids ensuring preservation of stereochemistry at C-25 and functional groups in the cyclic part was achieved with sodium chlorite catalyzed by TEMPO and bleach.

AB - A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3β-hydroxy-Δ5- or a Δ4-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3β-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides to sulfones prepared from (2R)- and (2S)-3-hydroxy-2-methylpropanoates. Oxidation of intermediate 26-alcohols into the corresponding carboxylic acids ensuring preservation of stereochemistry at C-25 and functional groups in the cyclic part was achieved with sodium chlorite catalyzed by TEMPO and bleach.

KW - 26-Hydroxycholesterol

KW - Biosynthesis

KW - Cholestenoic acids

KW - Cholic acids

UR - http://www.scopus.com/inward/record.url?scp=19344363060&partnerID=8YFLogxK

U2 - 10.1016/j.steroids.2005.02.014

DO - 10.1016/j.steroids.2005.02.014

M3 - Article

C2 - 15894040

AN - SCOPUS:19344363060

SN - 0039-128X

VL - 70

SP - 551

EP - 562

JO - STEROIDS

JF - STEROIDS

IS - 8

ER -

Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this