Chinese Journal of Magnetic Resonance >
Nuclear Magnetic Resonance Assignment and Crystal Structure of 3, 22-Dihydroxyhopane
Received date: 2020-06-29
Online published: 2020-08-27
Pure α- and β- isomers of 3, 22-dihydroxyhopane were obtained by the reduction of hydroxyl protected hydroxyhopanone with L-selectride. The absolute configuration of 3β, 22-hydroxyhopane was confirmed by single crystal X-ray diffraction, and the unambiguous 1H and 13C NMR data of two isomers were fully assigned for the first time. The preparation method is suitable for the separation of other unseparated α, β-isomers.
Key words： 3, 22-dihydroxyhopane; 1H NMR; 13C NMR; absolute configuration
Lei JIANG , Yang FU , Wen-wen GUO , Guo ZHENG , Qiang WANG . Nuclear Magnetic Resonance Assignment and Crystal Structure of 3, 22-Dihydroxyhopane[J]. Chinese Journal of Magnetic Resonance, 2021 , 38(2) : 255 -267 . DOI: 10.11938/cjmr20202840
| 1 | HUI W H , KO P D S , LEE Y C , et al. Triterpenoids from ten Lithocarpus species of HongKong[J]. Phytochemistry, 1975, 14, 1063- 1066. |
| 2 | TANAKA R , MATSUNAGA S . Saturated hopane and gammacerane triterpene-diols from the stem bark of Abies Veitchii[J]. Phytochemistry, 1992, 31, 3535- 3539. |
| 3 | HUI W H , LI M M . Six new triterpenoids and other triterpenoids and steroids from three Quercus species of HongKong[J]. J Chem Soc, 1977, Perkin Trans. Ⅰ, 897- 904. |
| 4 | ARTHUR H R , KO P D S . 3β, 22-dihydroxyhopane and other constituents from the leaves of Castanopsis Eyrei Tutch. of HongKong[J]. Aust J Chem, 1968, 21, 2583- 2584. |
| 5 | TANAKA R , MIZOTA T , MATSUNAGA S . Saturated gammaceranes from the stem bark of Abies MariesII[J]. J Nat Prod, 1994, 57, 761- 766. |
| 6 | HUI W H , LI M M . Structures of eight new triterpenoids and isolation of other triterpenoids and epi-ikshusterol from the stems of Lithocarpus cornea[J]. J Chem Soc, 1976, Perkin Trans. Ⅰ, 23- 30. |
| 7 | ?ERNY J , VYSTR?IL A , HUNECK S . über ein neues triterpen aus Dammar-Harz[J]. Chem Ber, 1963, 96, 3021- 3023. |
| 8 | HOSHINO T , NAKANO S , KONDO T , et al. Squalene-hopene cyclase: final deprotonation reaction, conformational analysis for the cyclization of (3R, S)-2, 3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the 5-membered E-ring[J]. Org Biomol Chem, 2004, 2, 1456- 1470. |
| 9 | WANG Q , LI Y J , ZHENG L Y , et al. Novel betulinic acid-nucleoside hybrids with potent anti-HIV activity[J]. ACS Med Chem Lett, 2020, 11, 2290- 2293. |
| 10 | WANG Q , HU W D , WANG S Y , et al. Synthesis of new 2'-deoxy-2'-fluoro-4'-azido nucleoside analogues as potent anti-HIV agents[J]. Euro J Med Chem, 2011, 46, 4178- 4183. |
| 11 | SATO T , HOSHINO T . Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site-directed mutagenesis experiments: initiation site of the polycyclization reaction and stabilization site of the carbocation intermediate of the initially cyclized a-ring[J]. Biosci Biotechnol Biochem, 1999, 63, 2189- 2198. |
/
| 〈 |
|
〉 |