title: Occurrence of Enantioselectivity in Nature: The Case of (S)-Norcoclaurine.
abstract: This review article is aimed at providing a monographic overview on (S)-norcoclaurine (NC) alkaloid from three diverse points of view, collected all together for the first time: 1) the synthetic one, where the compound is seen as a target chiral molecule to be obtained in the highest optical purity and as a starting point for the development of biocatalytic asymmetric syntheses of tetrahydroisoquinoline alkaloids; 2) the chromatographic one, which addresses the HPLC separation of the two NC enantiomers; and 3) the biochemical one, for which a thorough understanding of the topology and mechanism of action of norcoclaurine synthase (NCS) enzyme is still a matter of debate. Special emphasis on the most recent studies in the field is given by discussing the results published by the main research groups who are working on NC and NCS.
authors.affiliation: Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Rome, Italy.
authors.forename: Francesca
authors.initials: F
authors.lastname: Ghirga
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, Rome, Italy.
authors.forename: Deborah
authors.initials: D
authors.lastname: Quaglio
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, Rome, Italy.
authors.forename: Patrizio
authors.initials: P
authors.lastname: Ghirga
authors.affiliation: Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Rome, Italy.
authors.forename: Simone
authors.initials: S
authors.lastname: Berardozzi
authors.affiliation: Dipartimento di Scienze Biomolecolari, Università degli Studi di Urbino "Carlo Bo", Urbino, Italy.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Zappia
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, Rome, Italy.
authors.forename: Bruno
authors.initials: B
authors.lastname: Botta
authors.affiliation: Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Rome, Italy.
authors.forename: Mattia
authors.initials: M
authors.lastname: Mori
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, Rome, Italy.
authors.forename: Ilaria
authors.initials: I
authors.lastname: D'Acquarica
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D055162:Biocatalysis; D001669:Biochemical Phenomena; D019731:Carbon-Nitrogen Ligases / Q000737:chemistry* / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D044005:Tetrahydroisoquinolines; D019731:Carbon-Nitrogen Ligases; C450500:norcoclaurine synthase; C012348:higenamine
keywords: chemoenzymatic synthesis; enantioselective HPLC; enantioselective synthesis; norcoclaurine; norcoclaurine synthase