SynBio‐SynChem Approaches to Diversifying the Pacidamycins through the Exploitation of an Observed Pictet‐Spengler Reaction
Sign Up to like & getrecommendations! Published in 2020 at "Chembiochem"
DOI: 10.1002/cbic.202000594
Abstract: A nonenzymatic Pictet‐Spengler reaction has been postulated to give rise to a subset of naturally occurring uridyl peptide antibiotics (UPAs). Here, using a combination of strain engineering and synthetic chemistry, we demonstrate that Pictet‐Spengler chemistry… read more here.
Keywords: spengler reaction; spengler; chemistry; pictet spengler ... 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
A Catalytic Asymmetric Pictet–Spengler Platform as a Biomimetic Diversification Strategy toward Naturally Occurring Alkaloids
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c06664
Abstract: Tetrahydroisoquinoline (THIQ) alkaloids constitute a large and diverse class of bioactive natural products, with the parent compounds and related downstream biosynthetic secondary metabolites spanning thousands of isolated structures. Chemoenzymatic synthetic approaches toward the relevant THIQs… read more here.
Keywords: asymmetric pictet; pictet spengler; spengler platform; catalytic asymmetric ... See more keywords
Enzyme catalysed Pictet-Spengler formation of chiral 1,1'-disubstituted- and spiro-tetrahydroisoquinolines
Sign Up to like & getrecommendations! Published in 2017 at "Nature Communications"
DOI: 10.1038/ncomms14883
Abstract: The Pictet–Spengler reaction (PSR) involves the condensation and ring closure between a β-arylethylamine and a carbonyl compound. The combination of dopamine and ketones in a PSR leads to the formation of 1,1′-disubstituted tetrahydroisoquinolines (THIQs), structures… read more here.
Keywords: chiral disubstituted; pictet spengler; enzyme catalysed; disubstituted spiro ... See more keywords
Mechanism and origins of selectivity in the enantioselective oxa-Pictet–Spengler reaction: a cooperative catalytic complex from a hydrogen bond donor and chiral phosphoric acid†
Sign Up to like & getrecommendations! Published in 2020 at "Chemical Science"
DOI: 10.1039/d0sc03250f
Abstract: Enantioselective additions to oxocarbenium ions are high-value synthetic transformations but have proven challenging to achieve. In particular, the oxa-Pictet–Spengler reaction has only recently been rendered enantioselective. We report experimental and computational studies on the mechanism… read more here.
Keywords: spengler reaction; hydrogen; hydrogen bond; pictet spengler ... See more keywords