Uncovering the Mechanism of Azepino‐Indole Skeleton Formation via Pictet–Spengler Reaction by Strictosidine Synthase: A Quantum Chemical Investigation
Sign Up to like & getrecommendations! Published in 2023 at "ChemistryOpen"
DOI: 10.1002/open.202300043
Abstract: Abstract Strictosidine synthase (STR) catalyzes the Pictet–Spengler (PS) reaction of tryptamine and secologanin to produce strictosidine. Recent studies demonstrated that the enzyme can also catalyze the reaction of non‐natural substrates to form new alkaloid skeletons.… read more here.
Keywords: azepino indole; reaction; strictosidine synthase; indole skeleton ... See more keywords
β-Methyltryptamine Provoking the Crucial Role of Strictosidine Synthase Tyr151-OH for Its Stereoselective Pictet-Spengler Reactions to Tryptoline-type Alkaloids.
Sign Up to like & getrecommendations! Published in 2022 at "ACS chemical biology"
DOI: 10.1021/acschembio.1c00844
Abstract: Strictosidine synthase (STR), the gate enzyme for monoterpenoid indole alkaloid biosynthesis, catalyzes the Pictet-Spengler reaction (PSR) of various tryptamine derivatives with secologanin assisted by "indole sandwich" stabilization. Continuous exploration with β-methyltryptamine (IPA) stereoselectively delivered the… read more here.
Keywords: role; pictet spengler; tyr151; strictosidine synthase ... See more keywords
Strictosidine Synthase Triggered Enantioselective Synthesis of N-Substituted (S)-3,14,18,19-Tetrahydroangustines as Novel Topoisomerase I Inhibitors.
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DOI: 10.1021/acschembio.7b00740
Abstract: Monoterpenoid indole alkaloids (MIAs) comprise an important class of molecules for drug discovery, and they have variant carbon skeletons with prominent bioactivities. For instance, in spite of limitations to their use, camptothecins are the only… read more here.
Keywords: synthase triggered; top1; triggered enantioselective; strictosidine synthase ... See more keywords