61219-76-9Relevant articles and documents
Synthesis of deuterated mevalonolactone isotopomers
Dickschat, Jeroen S.,Citron, Christian A.,Brock, Nelson L.,Riclea, Ramona,Kuhz, Henning
experimental part, p. 3339 - 3346 (2011/08/03)
A synthetic route was developed for the preparation of deuterated mevalonolactones. Using low-cost deuterated reagents, this route allows for the independent introduction of deuterium labeling into any carbon position or into any combination of positions. Following this approach, the synthesis of [6,6,6-2H3]mevalonolactone, [4,4,6,6,6-2H 5]mevalonolact-one, [5,5-2H2]mevalonolactone, [5,5,6,6,6-2H5]mevalonolact-one, and [2,2,6,6,6- 2H5]mevalonolactone is described.
Practical synthesis of [3-(2H3)methyl]mevalonolactone and incorporation experiment of [3-(2H3)methyl]mevalonolactone and [13C]labeled acetate in the biosynthesis of isoprenoidal diether lipids of halophilic archaea
Yamauchi,Natsubori,Murae
, p. 2513 - 2519 (2007/10/03)
The biosynthesis of the saturated isoprenoid portion of membrane lipids of the halophilic archaea Natrinema pallidum was investigated. At first, a practical method for the synthesis of [3-(2H3)methyl]mevalonate was developed. Then, incorporation experiments of [3-(2H3)methyl]mevalonate into the lipid core indicated that the isoprenoid portion was derived from mevalonate. However, a [2-13C]acetate-incorporation experiment revealed a significant difference in the degree of 13C enrichment between the expected position from the mevalonate pathway, the CH2 groups (and at one terminal CH3 group) and the CH3 groups in the saturated isoprenoid chain. These results suggest that (1) the mevalonate pathway exists and is active, and (2) a part of acetoacetyl-CoA is not derived from an acetate in the biosynthesis of the isoprenoidal lipid-core of the archaebacterium.
Ring D Expansion and Aromatisation in the Biosynthesis of Nic-1, an Antifeedant Steroid from Nicandra physaloides
Gill, Harjit K.,Smith, Roland W.,Whiting, Donald A.
, p. 2989 - 2993 (2007/10/02)
Isotope administration experiments with Nicandra physaloides plants using 2H3>- and 14C3>-mevalonic acid, analysed by 2H NMR and by degradation, respectively, show that the aromatic ring-D of Nic-1 (2) is formed by ring-D expansion in a steroid precursor with oxidative inclusion of the C/D angular methyl.