Synthesis of deuterated isopentyl pyrophosphates for chemo-enzymatic labelling methods: GC-EI-MS based 1,2-hydride shift in epicedrol biosynthesis

TitleSynthesis of deuterated isopentyl pyrophosphates for chemo-enzymatic labelling methods: GC-EI-MS based 1,2-hydride shift in epicedrol biosynthesis
Publication TypeJournal Article
Year of Publication2019
AuthorsSaid, MS, Navale, GR, Gajbhiye, JM, Shinde, SS
JournalRSC Advances
Volume9
Issue48
Pagination 28258-28261
Date PublishedSEP
Type of ArticleArticle
Abstract

A sesquiterpene epicedrol cyclase mechanism was elucidated based on the gas chromatography coupled to electron impact mass spectrometry fragmentation data of deuterated (H-2) epicedrol analogues. The chemo-enzymatic method was applied for the specific synthesis of 8-position labelled farnesyl pyrophosphate and epicedrol. EI-MS fragmentation ions compared with non-labelled and isotopic mass shift fragments suggest that the H-2 of C6 migrates to the C7 position during the cyclization mechanism.

DOI10.1039/c9ra00163h
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.049

Divison category: 
Organic Chemistry

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