THE BIOSYNTHESIS OF A NON-HEAD TO TAIL MONOTERPENE, ARTEMISIA KETONE
Abstract
Abstract Artemisia ketone (1) biosynthesized from [2-14C]mevalonic acid by Artemisia annua L. was found to contain 80% and 13% of the incorporated tracer in the internal and terminal methyls respectively. The unbalance of labelling means that the C5-precursors of two halves of (1) are enzymatically differentiated.
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Artemisia ketone is formed by a non-standard head-to-middle condensation of DMAPP, which is thought to proceed via chrysanthemyl pyrophosphate, an intermediate containing a three-membered ring.
“Artemisia ketone (276) is formed by a non-standard “head-to-middle” condensation of DMAPP [104,122,123,124,125,126], which is thought to proceed as shown in Scheme 2 via chrysanthemyl pyrophosphate, an intermediate containing a three-membered ring.”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [122]
Cites
On the Occurrence of the Santolinenones. Terpenes. XV1
Zalkow, L. H., BRANNON, D. R., & Uecke, J. W. (1964) · The Journal of Organic Chemistry · doi:10.1021/jo01032a520 · Cited by 33 · see citing works
Terpenoids. IX. Biogenesis of some monoterpenoids not derived from a geranyl precursor
Bates, R. B., & Paknikar, S. K. (1965) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)90088-1 · Cited by 20 · see citing works
Takemoto, T., & Nakajima, T. (1957) · YAKUGAKU ZASSHI · doi:10.1248/yakushi1947.77.12_1339 · Cited by 6 · see citing works
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The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao)
Brown, G. D. (2010) · Molecules · doi:10.3390/molecules15117603 · Cited by 363 · see citing works
On the biosyntheses of artemisia ketone and bakuchiol
Risinger, G. E., Karimian, K., Jungk, S., & Simpson, J. B. (1978) · Experientia · doi:10.1007/bf01922903 · Cited by 11 · see citing works
- Authors
- Suga, T., Shishibori, T., Kotera, K., & Fujii, R.
- Affiliations
- Hiroshima University (JP)
- Venue
- Chemistry Letters
- Publisher
- Oxford University Press (OUP)
- Published
- 1972-07
- Volume
- 1
- Issue
- 7
- Pages
- 533-534
- ISSN
- 0366-7022 (ISSN-L)
- 1348-0715
- OpenAlex
- W2011754071
- Cited by
- 10
- References
- 3
- Citations by year
- 2014: 2
- FWCI
- 0.19
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemistry Letters (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant tissue culture and regeneration
- Keywords
- artemisia ketone, monoterpene biosynthesis, Artemisia annua, mevalonate, carbon-14 labeling, methyl group incorporation
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