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Unusual Acetylation‐Dependent Reaction Cascade in the Biosynthesis of the Pyrroloindole Drug Physostigmine 下载免费PDF全文
Joyce Liu Tailun Ng Dr. Zhe Rui Omer Ad Prof. Dr. Wenjun Zhang 《Angewandte Chemie (International ed. in English)》2014,53(1):136-139
Physostigmine is a parasympathomimetic drug used to treat a variety of neurological disorders, including Alzheimer’s disease and glaucoma. Because of its potent biological activity and unique pyrroloindole skeleton, physostigmine has been the target of many organic syntheses. However, the biosynthesis of physostigmine has been relatively understudied. In this study, we identified a biosynthetic gene cluster for physostigmine by genome mining. The 8.5 kb gene cluster encodes eight proteins (PsmA–H), seven of which are required for the synthesis of physostigmine from 5‐hydroxytryptophan, as shown by in vitro total reconstitution. Further genetic and enzymatic studies enabled us to delineate the biosynthetic pathway for physostigmine. The pathway features an unusual reaction cascade consisting of highly coordinated methylation and acetylation/deacetylation reactions. 相似文献
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S. Yu. Ryabova L. M. Alekseeva E. A. Lisitsa N. S. Masterova S. S. Kiselev M. I. Evstratova V. G. Granik 《Russian Chemical Bulletin》2006,55(12):2271-2277
Reactions of 2-(3,3-diamino-2-cyanoprop-2-enylidene)indolin-3-ones with amide acetals afforded derivatives of 3-aminomethyleneamino-2-cyano-9-oxo-9H-pyrrolo[1,2-a]indole and 3-amino-2-cyano-9-oxo-9H-pyrrolo[1,2-a]indole. The rate and pathway of the reaction depend on the reagents and solvents. The formation schemes for the compounds
obtained were proposed. Their structures were proven by IR and 1H NMR spectroscopy and mass spectrometry and confirmed by independent syntheses.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2186–2192, December, 2006. 相似文献
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Chenlong Zhu Zhaobo Liu Guanyu Chen Kai Zhang Prof. Dr. Hanfeng Ding 《Angewandte Chemie (International ed. in English)》2015,54(3):879-882
A concise total synthesis of rac‐alsmaphorazine D has been described for the first time. The efficient synthetic strategy features four key transformations: 1) a catalytic intramolecular oxidative cyclization for the δ‐lactamindole backbone; 2) an oxidative cyclic aminal formation for the hexahydropyrrolo[2,3‐b]pyrrole framework; 3) a transannular radical cyclization for the construction of the diazabicyclo[3.3.1]nonane structure; and 4) a one‐pot desilylation/double epimerization reaction that affirms the relative stereochemistry. 相似文献
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I. Sh. Chikvaidze Sh. A. Samsoniya N. Sh. Lomadze N. L. Targamadze Z. E. Saliya 《Chemistry of Heterocyclic Compounds》2000,36(12):1421-1425
During the E. Fischer type synthesis of 2,7-diethoxycarbonyl-1H,8H-pyrrolo[3,2-g]indole there was discovered an unusual chlorination reaction of the benzene ring in 7-amino-2-ethoxycarbonylindole. It is suggested that the reaction occurs via an electrophilic substitution mechanism. 相似文献
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