Preparation of (+)-trans-isoalliin and its isomers by chemical synthesis and RP-HPLC resolution.
Lasanthi Jayathilaka, Shalini Gupta, Jin-Sheng Huang, Jenny Lee, Bao-Shiang Lee
文献索引：J. Biomol. Tech. 25(3) , 67-76, (2014)
全文：HTML全文
摘要
Naturally occurring (+)-trans-isoalliin, (R(C)R(S))-(+)-trans-S-1-propenyl-L-cysteine sulfoxide, is a major cysteine sulfoxide in onion. The importance of producing it synthetically to support further research is very well recognized. The (+)-trans-isoalliin is prepared by chemical synthesis and reversed-phase (RP)-HPLC. First, S-2-propenyl-L-cysteine (deoxyalliin) is formed from L-cysteine and allyl bromide, which is then isomerized to S-1-propenyl-L-cysteine (deoxyisoalliin) by a base-catalyzed reaction. A mixture of cis and trans forms of deoxyisoalliin is formed and separated by RP-HPLC. Oxidation of the trans form of deoxyisoalliin by H2O2 produces a mixture of (-)- and (+)-trans-isoalliin. Finally, RP-HPLC is used successfully in separating (-)- and (+)-trans-isoalliin, and hence, (+)-trans-isoalliin is synthesized for the first time in this study. In addition, the (±) diastereomers of cis-isoalliin are also separated and purified by RP-HPLC.
相关化合物
相关文献：
2009-07-29
[J. Am. Chem. Soc. 131(29) , 9900-1, (2009)]
Structure Analysis of Poly (propylene-β-d oxide) by Proton Nuclear Magnetic Resonance Spectroscopy. Oguni N, et al.
[Macromolecules 6(3) , 459-465, (1973)]
cis-trans Isomerization of 1-Bromo-1-propene and Related Compounds. Harwell, KE and Hatch LF.
[J. Am. Chem. Soc. 77(6) , 1682-1684, (1955)]
Substituted Dienols from Palladium Catalyzed Coupling of Hydroaluminated Enynols with Aryl Iodides. Crook KE, et al.
[Lett. Org. Chem. 5(3) , 158-164, (2008)]
Facile synthesis of trans-S-1-propenyl-L-cysteine sulfoxide (isoalliin) in onions (Allium cepa). Lee S, et al.
[Bull. Korean Chem. Soc. 32 , 319-320, (2011)]