Synthesis of two isomers of 3-amino-7α-12α-dihydroxy-5β-cholanic acid
Aim.With the aim of differences investigation in physical-chemical properties optimized synthesis of the two stereoisomers of 3-amino-7-12-dihydroxycholanic acid has been performed. Methods and results.As the source compound natural cholic acid was used. 3α-amino-7α-12α-dihydroxy-5β-cholanic acid...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Zaporozhye State Medical University
2015-04-01
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| Series: | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| Subjects: | |
| Online Access: | http://pharmed.zsmu.edu.ua/article/view/41342/37758 |
| _version_ | 1818529766757629952 |
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| author | D. O. Barsuk S. M. Kovalenko |
| author_facet | D. O. Barsuk S. M. Kovalenko |
| author_sort | D. O. Barsuk |
| collection | DOAJ |
| description | Aim.With the aim of differences investigation in physical-chemical properties optimized synthesis of the two stereoisomers of 3-amino-7-12-dihydroxycholanic acid has been performed.
Methods and results.As the source compound natural cholic acid was used. 3α-amino-7α-12α-dihydroxy-5β-cholanic acid was obtained in high yield and low number of by-products. The yield of 3β-amino-7α-12α-dihydroxy-5β-cholanic acid was low because of steric interference and process needed additional treatment stages. Column chromatography was used for cleaning compounds. The structure was studied and confirmed by NMR method. Significant differences in signals of NMR spectra and physical-chemical properties 3β-amino-7α-12α-dihydroxy-5β-cholanic acid and 3α-amino-7α-12α-dihydroxy-5β-cholanic acid wasn’t found or observed. |
| first_indexed | 2024-12-11T17:11:08Z |
| format | Article |
| id | doaj.art-c22ed3314069428c89f0b352adfd803c |
| institution | Directory Open Access Journal |
| issn | 2306-8094 2409-2932 |
| language | English |
| last_indexed | 2024-12-11T17:11:08Z |
| publishDate | 2015-04-01 |
| publisher | Zaporozhye State Medical University |
| record_format | Article |
| series | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| spelling | doaj.art-c22ed3314069428c89f0b352adfd803c2022-12-22T00:57:32ZengZaporozhye State Medical UniversityAktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki2306-80942409-29322015-04-011222610.14739/2409-2932.2015.1.41342Synthesis of two isomers of 3-amino-7α-12α-dihydroxy-5β-cholanic acidD. O. Barsuk S. M. KovalenkoAim.With the aim of differences investigation in physical-chemical properties optimized synthesis of the two stereoisomers of 3-amino-7-12-dihydroxycholanic acid has been performed. Methods and results.As the source compound natural cholic acid was used. 3α-amino-7α-12α-dihydroxy-5β-cholanic acid was obtained in high yield and low number of by-products. The yield of 3β-amino-7α-12α-dihydroxy-5β-cholanic acid was low because of steric interference and process needed additional treatment stages. Column chromatography was used for cleaning compounds. The structure was studied and confirmed by NMR method. Significant differences in signals of NMR spectra and physical-chemical properties 3β-amino-7α-12α-dihydroxy-5β-cholanic acid and 3α-amino-7α-12α-dihydroxy-5β-cholanic acid wasn’t found or observed.http://pharmed.zsmu.edu.ua/article/view/41342/37758Cholic AcidStereoisomers3-amino-7α-12α-dihydroxy-5β-cholanic acid |
| spellingShingle | D. O. Barsuk S. M. Kovalenko Synthesis of two isomers of 3-amino-7α-12α-dihydroxy-5β-cholanic acid Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki Cholic Acid Stereoisomers 3-amino-7α-12α-dihydroxy-5β-cholanic acid |
| title | Synthesis of two isomers of 3-amino-7α-12α-dihydroxy-5β-cholanic acid |
| title_full | Synthesis of two isomers of 3-amino-7α-12α-dihydroxy-5β-cholanic acid |
| title_fullStr | Synthesis of two isomers of 3-amino-7α-12α-dihydroxy-5β-cholanic acid |
| title_full_unstemmed | Synthesis of two isomers of 3-amino-7α-12α-dihydroxy-5β-cholanic acid |
| title_short | Synthesis of two isomers of 3-amino-7α-12α-dihydroxy-5β-cholanic acid |
| title_sort | synthesis of two isomers of 3 amino 7α 12α dihydroxy 5β cholanic acid |
| topic | Cholic Acid Stereoisomers 3-amino-7α-12α-dihydroxy-5β-cholanic acid |
| url | http://pharmed.zsmu.edu.ua/article/view/41342/37758 |
| work_keys_str_mv | AT dobarsuk synthesisoftwoisomersof3amino7a12adihydroxy5bcholanicacid AT smkovalenko synthesisoftwoisomersof3amino7a12adihydroxy5bcholanicacid |