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1992 2
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17 results

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"Cation-Stitching Cascade": exquisite control of terpene cyclization in cyclooctatin biosynthesis.
Sato H, Teramoto K, Masumoto Y, Tezuka N, Sakai K, Ueda S, Totsuka Y, Shinada T, Nishiyama M, Wang C, Kuzuyama T, Uchiyama M. Sato H, et al. Sci Rep. 2015 Dec 18;5:18471. doi: 10.1038/srep18471. Sci Rep. 2015. PMID: 26681256 Free PMC article.
In this work, we describe an in-depth mechanistic study on cyclooctatin biosynthesis by means of theoretical calculations combined with experimental methods. We show that the main framework of cyclooctatin is formed through domino-type carbocation transportation alo …
In this work, we describe an in-depth mechanistic study on cyclooctatin biosynthesis by means of theoretical calculations combined wi …
Cloning and heterologous expression of the cyclooctatin biosynthetic gene cluster afford a diterpene cyclase and two p450 hydroxylases.
Kim SY, Zhao P, Igarashi M, Sawa R, Tomita T, Nishiyama M, Kuzuyama T. Kim SY, et al. Chem Biol. 2009 Jul 31;16(7):736-43. doi: 10.1016/j.chembiol.2009.06.007. Chem Biol. 2009. PMID: 19635410
Cyclooctatin, a diterpene characterized by a 5-8-5 fused ring system, is a potent inhibitor of lysophospholipase. Here we report the cloning and characterization of a complete cyclooctatin biosynthetic gene cluster from Streptomyces melanosporofaciens MI614-43F2 and …
Cyclooctatin, a diterpene characterized by a 5-8-5 fused ring system, is a potent inhibitor of lysophospholipase. Here we report the …
Current understanding and biotechnological application of the bacterial diterpene synthase CotB2.
Driller R, Garbe D, Mehlmer N, Fuchs M, Raz K, Major DT, Brück T, Loll B. Driller R, et al. Beilstein J Org Chem. 2019 Oct 2;15:2355-2368. doi: 10.3762/bjoc.15.228. eCollection 2019. Beilstein J Org Chem. 2019. PMID: 31666870 Free PMC article. Review.
CotB2 catalyzes the first committed step in cyclooctatin biosynthesis of the soil bacterium Streptomyces melanosporofaciens. To date, CotB2 represents the best studied bacterial diterpene synthase. ...
CotB2 catalyzes the first committed step in cyclooctatin biosynthesis of the soil bacterium Streptomyces melanosporofaciens. To date, …
The energetic viability of an unexpected skeletal rearrangement in cyclooctatin biosynthesis.
Hong YJ, Tantillo DJ. Hong YJ, et al. Org Biomol Chem. 2015 Nov 7;13(41):10273-8. doi: 10.1039/c5ob01785h. Org Biomol Chem. 2015. PMID: 26371548
Results of density functional theory calculations on possible mechanisms for formation of the diterpenoid cyclooctatin are described. These results are consistent with the involvement of an unexpected 1,3-alkyl shift that interconverts two cyclopropylcarbinyl carbocations …
Results of density functional theory calculations on possible mechanisms for formation of the diterpenoid cyclooctatin are described. …
Cyclooctatin, a new inhibitor of lysophospholipase, produced by Streptomyces melanosporofaciens MI614-43F2. Taxonomy, production, isolation, physico-chemical properties and biological activities.
Aoyagi T, Aoyama T, Kojima F, Hattori S, Honma Y, Hamada M, Takeuchi T. Aoyagi T, et al. J Antibiot (Tokyo). 1992 Oct;45(10):1587-91. doi: 10.7164/antibiotics.45.1587. J Antibiot (Tokyo). 1992. PMID: 1335449 Free article.
Cyclooctatin has been isolated from Streptomyces melanosporofaciens MI614-43F2 as part of a program designed to find microorganism-produced inhibitors of lysophospholipase. It was purified by chromatography on silica gel, Capcell Pak C18 (HPLC) and Sephadex LH-20 followed …
Cyclooctatin has been isolated from Streptomyces melanosporofaciens MI614-43F2 as part of a program designed to find microorganism-pr …
Theoretical Study of Natural Product Biosynthesis Using Computational Chemistry.
Sato H. Sato H. Chem Pharm Bull (Tokyo). 2024;72(6):524-528. doi: 10.1248/cpb.c24-00082. Chem Pharm Bull (Tokyo). 2024. PMID: 38825452 Free article. Review.
In this review, we will discuss the biosynthetic studies using computational chemistry for various terpene compounds such as cyclooctatin, sesterfisherol, quiannulatene, trichobrasilenol, asperterpenol, preasperterpenoid, spiroviolene, and mangicol....
In this review, we will discuss the biosynthetic studies using computational chemistry for various terpene compounds such as cyclooctatin …
Understanding the role of active site residues in CotB2 catalysis using a cluster model.
Raz K, Driller R, Brück T, Loll B, Major DT. Raz K, et al. Beilstein J Org Chem. 2020 Jan 8;16:50-59. doi: 10.3762/bjoc.16.7. eCollection 2020. Beilstein J Org Chem. 2020. PMID: 31976016 Free PMC article.
CotB2 is a diterpene cyclase from Streptomyces melanosporofaciens, which catalyzes the formation of cycloocta-9-en-7-ol, a precursor to the next-generation anti-inflammatory drug cyclooctatin. In this work, we present evidence for the significant role of the active site's …
CotB2 is a diterpene cyclase from Streptomyces melanosporofaciens, which catalyzes the formation of cycloocta-9-en-7-ol, a precursor to the …
The first structure of a bacterial diterpene cyclase: CotB2.
Janke R, Görner C, Hirte M, Brück T, Loll B. Janke R, et al. Acta Crystallogr D Biol Crystallogr. 2014 Jun;70(Pt 6):1528-37. doi: 10.1107/S1399004714005513. Epub 2014 May 23. Acta Crystallogr D Biol Crystallogr. 2014. PMID: 24914964
The subsequent oxidation of cyclooctat-9-en-7-ol by two cytochrome P450 monooxygenases leads to bioactive cyclooctatin. Plasticity residues that decorate the active site of CotB2 have been mutated, resulting in alternative monocyclic, dicyclic and tricyclic compounds that …
The subsequent oxidation of cyclooctat-9-en-7-ol by two cytochrome P450 monooxygenases leads to bioactive cyclooctatin. Plasticity re …
17 results