Steroidal Ribbons from (3 alpha,5 beta,20S)-3-Hycloxy-20-Methyl-Pregnan-21-oic Acid
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F16%3A00471227" target="_blank" >RIV/61389030:_____/16:00471227 - isvavai.cz</a>
Result on the web
<a href="http://www.eurekaselect.com/147510" target="_blank" >http://www.eurekaselect.com/147510</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1174/1570178614666161118161810" target="_blank" >10.1174/1570178614666161118161810</a>
Alternative languages
Result language
angličtina
Original language name
Steroidal Ribbons from (3 alpha,5 beta,20S)-3-Hycloxy-20-Methyl-Pregnan-21-oic Acid
Original language description
Background: Steroidal ribbons (or steroid containing ribbons) are being studied for several reasons, firstly, they may be included in the lipid bilayer, especially if they have suitable size (as "extended cholesterol"), and they are interesting in binding to steroidal receptors, gelators, and/or superassembly synthons. Bile acids seem to be very suitable as their components have natural tendency to form supramolecular assemblies. nMethods: Synthesis of ester bonded tetramer of (3 alpha,5 beta,20S)-3-Hycloxy-20-Methyl-Pregnan-2-oic acid was achieved using 2,6-dichlorobenzoyl chloride and DMAP in toluene. To prepare shortened side chain steroid, the oxidative decarboxylation of protected lithocholic acid was used, followed by oxidation of thus formed terminal double bond. Aggregation properties of the prepared steroidal ribbon were studied alone and after binding with copper(II) ions. nResults: There was synthesized 3 alpha-{3 alpha-{3 alpha-[(3 alpha,5(3,20S)-3-hydroxy-pregnane-20-carbonyBoxy] [(5 beta,20S)-pregnane-20-carbonyBoxyll-[(5 beta,20S)-pregnane-20-carbonyBoxyll-(5 beta,20S)pregnane-20carboxylate as a steroidal ribbon derived from bile acid, however, with the shortened side chain. The aggregation of the ribbon prepared in chloroform after binding of Cu(II) ions was monitored by absorption and circular dichroism spectroscopy at different ratios [tetramer]/[Cu(II)]. A positive bisignate band centered at 280 nm emerges; whose intensity increases with the [tetramer]/[Cu(II)] ratio. This result suggests that chiral aggregates are obtained as a consequence of Cu(II) complexation. Time dependent experiments did not show any variation in both UV-Vis and CD spectra. nConclusion: Prepared and documented new type of tetrasteroidal ribbon is unique one for the length of the connecting steroidal side chain. Its construction was done aiming to have more rigid ribbon than the one of lithocholic acid, and on the other hand, less rigid than the one derived from etieni...
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Letters in Organic Chemistry
ISSN
1570-1786
e-ISSN
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Volume of the periodical
13
Issue of the periodical within the volume
10
Country of publishing house
AE - UNITED ARAB EMIRATES
Number of pages
7
Pages from-to
711-717
UT code for WoS article
000391710500003
EID of the result in the Scopus database
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