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Literature DB >> 32442350

Germacrene A-A Central Intermediate in Sesquiterpene Biosynthesis.

Abstract

This review summarises known sesquiterpenes whose biosyntheses proceed through the intermediate germacrene A. First, the occurrence and biosynthesis of germacrene A in Nature and its peculiar chemistry will be highlighted, followed by a discussion of 6-6 and 5-7 bicyclic compounds and their more complex derivatives. For each compound the absolute configuration, if it is known, and the reasoning for its assignment is presented.

Entities: Chemical Disease Gene Mutation Species

Keywords: biosynthesis; configuration determination; enzyme catalysis; germacrene A; sesquiterpenes

Year: 2020 PMID： 32442350 PMCID： PMC7821278 DOI： 10.1002/chem.202002163

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

149 in total

1. Cytotoxic terpenoids from the Formosan soft coral Nephthea brassica.

Authors: C Y Duh; S K Wang; Y L Weng; M Y Chiang; C F Dai
Journal: J Nat Prod Date: 1999-11 Impact factor: 4.050

2. Inhibition of (+)-aristolochene synthase with iminium salts resembling eudesmane cation.

Authors: Juan A Faraldos; Rudolf K Allemann
Journal: Org Lett Date: 2011-01-27 Impact factor: 6.005

3. Structure and absolute configuration of kusunol.

Authors: H Hikino; N Suzuki; T Takemoto
Journal: Chem Pharm Bull (Tokyo) Date: 1968-05 Impact factor: 1.645

4. Secondary metabolites of Peucedanum tauricum fruits.

Authors: Hailemichael Tesso; Wilfried A König; Karl-Heinz Kubeczka; Magdalena Bartnik; Kazimierz Glowniak
Journal: Phytochemistry Date: 2005-03 Impact factor: 4.072

5. Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library.

Authors: Cinzia M Bertea; Alessandra Voster; Francel W A Verstappen; Massimo Maffei; Jules Beekwilder; Harro J Bouwmeester
Journal: Arch Biochem Biophys Date: 2006-03-15 Impact factor: 4.013

6. Correction of the structure of a new sesquiterpene from Cistus creticus ssp. creticus.

Authors: Konstantinos Hatzellis; Georgia Pagona; Apostolos Spyros; Costas Demetzos; Haralambos E Katerinopoulos
Journal: J Nat Prod Date: 2004-12 Impact factor: 4.050

7. Synthetic efficiency in enzyme mechanisms involving carbocations: aristolochene synthase.

Authors: Rudolf K Allemann; Neil J Young; Shuhua Ma; Donald G Truhlar; Jiali Gao
Journal: J Am Chem Soc Date: 2007-10-05 Impact factor: 15.419

8. Diversity in cyclic sesquiterpene production by Gossypium hirsutum.

Authors: H J Williams; I Sattler; G Moyna; A I Scott; A A Bell; S B Vinson
Journal: Phytochemistry Date: 1995-12 Impact factor: 4.072

9. Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120.

Authors: Sean A Agger; Fernando Lopez-Gallego; Thomas R Hoye; Claudia Schmidt-Dannert
Journal: J Bacteriol Date: 2008-07-25 Impact factor: 3.490

10. Quantitative exploration of the catalytic landscape separating divergent plant sesquiterpene synthases.

Authors: Paul E O'Maille; Arthur Malone; Nikki Dellas; B Andes Hess; Lidia Smentek; Iseult Sheehan; Bryan T Greenhagen; Joe Chappell; Gerard Manning; Joseph P Noel
Journal: Nat Chem Biol Date: 2008-09-07 Impact factor: 15.040

3 in total

Review 1. Germacrene A-A Central Intermediate in Sesquiterpene Biosynthesis.

Authors: Houchao Xu; Jeroen S Dickschat
Journal: Chemistry Date: 2020-09-30 Impact factor: 5.236

Review 2. Hedycaryol - Central Intermediates in Sesquiterpene Biosynthesis, Part II.

Authors: Houchao Xu; Jeroen S Dickschat
Journal: Chemistry Date: 2022-03-21 Impact factor: 5.020

3. The enzyme mechanism of patchoulol synthase.

Authors: Houchao Xu; Bernd Goldfuss; Gregor Schnakenburg; Jeroen S Dickschat
Journal: Beilstein J Org Chem Date: 2022-01-03 Impact factor: 2.883

3 in total