Racemization mechanism of lithium tert-butylphenylphosphido-borane: A kinetic insight.
Sign Up to like & getrecommendations! Published in 2021 at "Chirality"
DOI: 10.1002/chir.23383
Abstract: The racemization mechanism of tert-butylphenylphosphido-borane is investigated experimentally and theoretically. Based on this converging approach, it is shown, first, that several phosphido-borane molecular species coexist at the time of the reaction and, second, that one… read more here.
Keywords: racemization mechanism; racemization; borane; butylphenylphosphido borane ... See more keywords
Enantioseparation and racemization of 3-fluorooxindoles.
Sign Up to like & getrecommendations! Published in 2023 at "Chirality"
DOI: 10.1002/chir.23572
Abstract: Fluorinated oxindoles are frequently used building blocks in asymmetric synthesis and represent an important scaffold found in a variety of biologically relevant compounds. While it is understood that incorporation of fluorine atoms into organic molecules… read more here.
Keywords: enantioseparation racemization; racemization fluorooxindoles; racemization;
Phenylglycine racemization in Fmoc-based solid-phase peptide synthesis: Stereochemical stability is achieved by choice of reaction conditions
Sign Up to like & getrecommendations! Published in 2017 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2017.04.047
Abstract: Abstract Phenylglycine-containing peptides have broad applications in medicinal chemistry, but their synthetic accessibility is complicated by the risk of epimerization during solid-phase peptide synthesis (SPPS). Phenylglycine is therefore often considered a troublesome residue. This work… read more here.
Keywords: racemization; solid phase; peptide synthesis; phase peptide ... See more keywords
Lipase/Oxovanadium Co-Catalyzed Dynamic Kinetic Resolution of Propargyl Alcohols: Competition between Racemization and Rearrangement.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b00334
Abstract: Quantitative conversion of racemic propargyl alcohols into optically active propargyl esters with up to 99% ee has been achieved by lipase/oxovanadium co-catalyzed dynamic kinetic resolution, which combines the lipase-catalyzed enantioselective esterification of the racemic substrates… read more here.
Keywords: lipase oxovanadium; racemization; propargyl alcohols; oxovanadium catalyzed ... See more keywords
Theoretical Study on the Epimerization of Azlactone Rings: Keto–Enol Tautomerism or Base-Mediated Racemization?
Sign Up to like & getrecommendations! Published in 2018 at "ACS Omega"
DOI: 10.1021/acsomega.8b00060
Abstract: Azlactones are versatile heterocycles employed in a diversity of transformations; the main drawback of these cycles consists in the epimerization of the α-carbonyl stereocenter during its preparation. We hereby present a theoretical study to explain… read more here.
Keywords: tautomerism base; theoretical study; racemization; keto enol ... See more keywords
Synthetic chiral molecular nanographenes: the key figure of the racemization barrier.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d1cc06561k
Abstract: Chirality is one of the most intriguing concepts of chemistry, involving living systems and, more recently, materials science. In particular, the bottom-up synthesis of molecular nanographenes endowed with one or several chiral elements is a… read more here.
Keywords: chiroptical properties; nanographenes key; molecular nanographenes; chiral molecular ... See more keywords
Evidence for sodium-rich alkaline water in the Tagish Lake parent body and implications for amino acid synthesis and racemization
Sign Up to like & getrecommendations! Published in 2020 at "Proceedings of the National Academy of Sciences of the United States of America"
DOI: 10.1073/pnas.2003276117
Abstract: Understanding the timing and mechanisms of amino acid synthesis and racemization on asteroidal parent bodies is key to demonstrating how amino acids evolved to be mostly left-handed in living organisms on Earth. It has been… read more here.
Keywords: synthesis racemization; amino acid; racemization; tagish lake ... See more keywords
Transient chirality inversion during racemization of a helical cobalt(III) complex
Sign Up to like & getrecommendations! Published in 2022 at "Proceedings of the National Academy of Sciences of the United States of America"
DOI: 10.1073/pnas.2113237119
Abstract: Significance We first observed a transient chirality inversion on a simple unimolecular platform during the racemization of a chiral helical complex [LCo3A6]3+, i.e., the helicity changed from P-rich (right-handed) to M-rich (left-handed), which then racemized… read more here.
Keywords: chirality inversion; time; transient chirality; racemization ... See more keywords
The problem of racemization in drug discovery and tools to predict it
Sign Up to like & getrecommendations! Published in 2019 at "Expert Opinion on Drug Discovery"
DOI: 10.1080/17460441.2019.1588881
Abstract: ABSTRACT Introduction: Racemization has long been an ignored risk in drug development, probably because of a lack of convenient access to good tools for its detection and an absence of methods to predict racemization risk.… read more here.
Keywords: drug; racemization risk; drug discovery; racemization ... See more keywords
Racemization rate and biomolecular characterization of D-serine synthesizing bacteria Bacillus tequilensis A1C1.
Sign Up to like & getrecommendations! Published in 2023 at "Letters in applied microbiology"
DOI: 10.1093/lambio/ovac017
Abstract: D-amino acids, the important components of the bacterial cell walls, are valuable molecular and genetic markers of bacterial-derived organic material in the environment. D-serine, a racemization product of L-serine is one such amino acid present… read more here.
Keywords: bacillus tequilensis; racemization rate; biomolecular characterization; serine ... See more keywords
Application of Racemization Process to Dynamic Resolution of (RS)-Phenylephrine to (R)-Phenylephrine β-D-Glucoside by Nicotiana tabacum Glucosyltransferase
Sign Up to like & getrecommendations! Published in 2018 at "Natural Product Communications"
DOI: 10.1177/1934578x1801301113
Abstract: Enzymatic glucosylation of racemic phenylephrine by glucosyltransferase from Nicotiana tabacum gave (R)-phenylephrine glucoside and recovered (S)-phenylephrine. [RuCl2(p-cymene)]2 complex associated with simple hemisalen ligands or zeolite were able to racemize (S)-phenylephrine. The [RuCl2(p-cymene)]2/Ligand/TEMPO or zeolite racemization… read more here.
Keywords: racemization; glucosyltransferase; nicotiana tabacum; phenylephrine ... See more keywords