APPLICATIONS in ASYMMETRIC SYNTHESIS Carlos
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Chiral Resolution Screening and Purification Kits Brochure
Maybridge Chiral Resolution Screening and Purification Kits Offering rapid access to optically pure chiral compounds Maybridge Chiral Resolution Screening and Purification Kits Introduction Diastereomeric crystallization is a commonly used effective process to obtain optically pure chiral compounds from their racemic mixtures. However, choosing the optimal conditions for the process; e.g., combination of resolving agents and solvents, is time-consuming, tedious and labor-intensive. Maybridge Chiral Resolution Screening and Purification kits provide scientists with a quick and systematic approach to find the best separation conditions under which the target compound can be isolated with the highest yield and optical purity. Key features and benefits • Rapid Screening – the kits include 384 different combinations of resolving agents and solvents, increasing the chances of finding the optimal separation conditions • High Performance – development time reduced to one day • Efficient – as little as 0.4mmol of racemate required • Ready to Use – resolving agents and solvents are pre-dispensed in 96-well plates • Convenient – the screening kits provide positive results identifiable by a quick visual or optical inspection, and the purification and recovery kit allows easy recovery and purification of the enantiomers Types of Chiral Resolution Screening and Purification Kits Amount Plate Product name Description Selection guide racemate Product code type required Maybridge Chiral • 4 x 96 plates containing 32 different acidic Identifies optimal -
Chiral Auxiliaries and Optical Resolving Agents
Chiral Auxiliaries and Optical Resolving Agents Most bioactive substances are optically active. For instance, if This brochure introduces a variety of chiral auxiliaries and a substance is synthesized as a racemic compound, its optical resolving agents. We hope that it will be useful for your enantiomer may show no activity or even undesired bioactivity. research of the synthesis of optically active compounds. Thus, methods to gain enantiopure compounds have been Additionally, TCI has some brochures introducing chiral developed. When synthesizing enantiopure compounds, the compounds for the chiral pool method in “Chiral Building Blocks”, methods are roughly divided into three methods. “Terpenes”, “Amino Acids” and other brochures. Sugar derivatives are also introduced in a catalog, “Reagents for Glyco Chemistry Chiral pool method: & Biology”, and category pages of sugar chains. Furthermore, The method using an easily available chiral compound as a TCI has many kinds of catalysts for asymmetric synthesis and starting material like an amino acid or sugar. introduce them in brochures such as “Asymmetric Synthesis” and Asymmetric synthesis: “Asymmetric Organocatalysts”, and other contents. The method to introduce an asymmetric point to compounds You can search our information through “asymmetric synthesis” without an asymmetric point. Syntheses using achiral as a keyword. auxiliaries are included here. Optical resolution: The method to separate a racemic compound into two ● Reactions with Chiral Auxiliaries enantiomers. The direct method using a chiral column and One of the most famous named reactions using chiral auxiliaries1) the indirect method to separate two enantiomers using is the Evans aldol reaction.2) This reaction is quite useful because optical resolving agents to convert into diastereomers are this reaction can efficiently introduce two asymmetric carbons into examples. -
Cross-Linked Protein Crystal Technology in Bioseparation and Biocatalytic Applications
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Aaltodoc Helsinki University of Technology, Department of Chemical Technology Technical Biochemistry Report 1/2004 Espoo 2004 TKK-BE-8 CROSS-LINKED PROTEIN CRYSTAL TECHNOLOGY IN BIOSEPARATION AND BIOCATALYTIC APPLICATIONS Antti Vuolanto Dissertation for the degree of Doctor in Science in Technology to be presented with due permission of the Department of Chemical Technology for public examination and debate in Auditorium KE 2 (Komppa Auditorium) at Helsinki University of Technology (Espoo, Finland) on the 20th of August, 2004, at 12 noon. Helsinki University of Technology Department of Chemical Technology Laboratory of Bioprocess Engineering Teknillinen korkeakoulu Kemian osasto Bioprosessitekniikan laboratorio Distribution: Helsinki University of Technology Laboratory of Bioprocess Engineering P.O. Box 6100 FIN-02015 HUT Tel. +358-9-4512541 Fax. +358-9-462373 E-mail: [email protected] ©Antti Vuolanto ISBN 951-22-7176-1 (printed) ISBN 951-22-7177-X (pdf) ISSN 0359-6621 Espoo 2004 Vuolanto, Antti. Cross-linked protein crystal technology in bioseparation and biocatalytic applications. Espoo 2004, Helsinki University of Technology. Abstract Chemical cross-linking of protein crystals form an insoluble and active protein matrix. Cross-linked protein crystals (CLPCs) have many excellent properties including high volumetric activity and stability. In this thesis CLPC technology was studied in bioseparation and biocatalytic applications. A novel immunoaffinity separation material, cross-linked antibody crystals (CLAC), was developed in this thesis for enantiospecific separation of a chiral drug, finrozole. Previously, the preparation of an antibody Fab fragment ENA5His capable of enantiospecific affinity separation of the chiral drug has been described. -
Page 1 of 108 RSC Advances
RSC Advances This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. This Accepted Manuscript will be replaced by the edited, formatted and paginated article as soon as this is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/advances Page 1 of 108 RSC Advances Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis Majid M. Heravi,* Vahideh Zadsirjan, Behnaz Farajpour Department of Chemistry, School of Science, Alzahra University, Vanak, Tehran, Iran Email: [email protected] Abstract Various chiral oxazolidinones (Evans' oxazolidinones) have been employed as effective chiral auxiliaries in the asymmetric alkylation of different enolates. This strategy has been found promising and successful when used as key step (steps) in the total synthesis of several biologically active natural products. In this report, we try to underscore the applications of Manuscript oxazolidinones as chiral auxiliary in asymmetric alkylation, and particularly in crucial chiral inducing steps in the total synthesis of natural products, showing biological activities. -
Enzyme Supported Crystallization of Chiral Amino Acids
ISBN 978-3-89336-715-3 40 Band /Volume Gesundheit /Health 40 Gesundheit Enzyme supported crystallization Health Kerstin Würges of chiral amino acids Mitglied der Helmholtz-Gemeinschaft Kerstin Würges Kerstin aminoacids Enzyme supported ofchiral crystallization Schriften des Forschungszentrums Jülich Reihe Gesundheit / Health Band / Volume 40 Forschungszentrum Jülich GmbH Institute of Bio- and Geosciences (IBG) Biotechnology (IBG-1) Enzyme supported crystallization of chiral amino acids Kerstin Würges Schriften des Forschungszentrums Jülich Reihe Gesundheit / Health Band / Volume 40 ISSN 1866-1785 ISBN 978-3-89336-715-3 Bibliographic information published by the Deutsche Nationalbibliothek. The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available in the Internet at http://dnb.d-nb.de. Publisher and Forschungszentrum Jülich GmbH Distributor: Zentralbibliothek 52425 Jülich Phone +49 (0) 24 61 61-53 68 · Fax +49 (0) 24 61 61-61 03 e-mail: [email protected] Internet: http://www.fz-juelich.de/zb Cover Design: Grafische Medien, Forschungszentrum Jülich GmbH Printer: Grafische Medien, Forschungszentrum Jülich GmbH Copyright: Forschungszentrum Jülich 2011 Schriften des Forschungszentrums Jülich Reihe Gesundheit / Health Band / Volume 40 D 61 (Diss. Düsseldorf, Univ., 2011) ISSN 1866-1785 ISBN 978-3-89336-715-3 The complete volume ist freely available on the Internet on the Jülicher Open Access Server (JUWEL) at http://www.fz-juelich.de/zb/juwel Neither this book nor any part of it may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilming, and recording, or by any information storage and retrieval system, without permission in writing from the publisher. -
Chapter 8. Chiral Catalysts José M
Chapter 8. Chiral Catalysts José M. Fraile, José I. García, José A. Mayoral 1. The Origin of Enantioselectivity in Catalytic Processes: the Nanoscale of Enantioselective Catalysis. Enantiomerically pure compounds are extremely important in fields such as medicine and pharmacy, nutrition, or materials with optical properties. Among the different methods to obtain enantiomerically pure compounds, asymmetric catalysis1 is probably the most interesting and challenging, in fact one single molecule of chiral catalyst can transfer its chiral information to thousands or even millions of new chiral molecules. Enantioselective reactions are the result of the competition between different possible diastereomeric reaction pathways, through diastereomeric transition states, when the prochiral substrate complexed to the chiral catalyst reacts with the corresponding reagent. The efficiency of the chirality transfer, measured as enantiomeric excess [% ee = (R−S)/(R+S) × 100], depends on electronic and steric factors in a very subtle form. A simple calculation shows that differences in energy of only 2 kcal/mol between these transition states are enough to obtain more than 90% ee, and small changes in any of the participants in the catalytic process can modify significantly this difference in energy. Those modifications may occur in the near environment of the catalytic centre, at less than 1 nm scale, but also at longer distances in the catalyst, substrate, reagent, solvent, or support in the case of immobilized catalysts. This is the reason because asymmetric -
Application of Chiral Sulfoxides in Asymmetric Synthesis
MOJ Bioorganic & Organic Chemistry Review Article Open Access Application of chiral sulfoxides in asymmetric synthesis Abstract Volume 2 Issue 2 - 2018 Chiral sulfoxides are used as a toolbox for the synthesis of enantiomeric/diastereomeric compounds, which are used as precursors for the pharmaceutically/chemically Ganapathy Subramanian Sankaran,1 important molecules. The current review focuses on applying these chiral sulfoxides Srinivasan Arumugan,2 Sivaraman towards the synthesis of the compounds having stereogenic center. In general, the 3 stereogenic center induced by the sulfoxide is able to direct the stereochemistry of Balasubramaniam 1University of Massachusetts Medical School, USA further transformation necessary to complete the total synthesis of bioactive molecules. 2Department of Science and Humanity (Chemistry), Karunya The nature of the reactive conformation of the sulfoxide is strongly dependent on the Institute of Technology and Sciences, India nature of the substituents at C-α and/or C-β. 3Indian Institute of Technology Madras, Chennai, India Correspondence: Sivaraman Balasubramaniam, Senior Research Scientist, Indian Institute of Technology Madras, Chennai, India, Tel +9177 1880 5113, Email [email protected] Received: March 07, 2018 | Published: March 29, 2018 Introduction occurred in a further oxidation step of one of the sulfinyl enantiomer to sulfone.13 The titanium-binaphthol complex catalyzes not only the Over the last three decades, the sulfinyl group has received asymmetric oxidation but also the kinetic -
Enantiomeric Resolution and Absolute Configuration of a Chiral Δ-Lactam
molecules Article Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam, Useful Intermediate for the Synthesis of Bioactive Compounds 1, 1, 1 1 Roberta Listro y, Giacomo Rossino y, Serena Della Volpe , Rita Stabile , Massimo Boiocchi 2 , Lorenzo Malavasi 3, Daniela Rossi 1,* and Simona Collina 1 1 Department of Drug Sciences, University of Pavia, via Taramelli 12, 27100 Pavia, Italy; [email protected] (R.L.); [email protected] (G.R.); [email protected] (S.D.V.); [email protected] (R.S.); [email protected] (S.C.) 2 Centro Grandi Strumenti, University of Pavia, via Bassi 21, 27100 Pavia, Italy; [email protected] 3 Department of Chemistry, University of Pavia, via Taramelli 12, 27100 Pavia, Italy; [email protected] * Correspondence: [email protected] These authors contributed equally to this work. y Academic Editor: Józef Drabowicz Received: 2 December 2020; Accepted: 18 December 2020; Published: 19 December 2020 Abstract: During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (trans-1). For the preparation of racemic trans-1, the Castagnoli-Cushman reaction was employed. (Semi)-preparative enantioselective HPLC allowed to obtain enantiomerically pure trans-1 whose absolute configuration was assigned by X-ray diffractometry. Compound (+)-(2R,3R)-1 represents a reference compound for the configurational study of structurally related lactams. -
Spherezymes: a Novel Structured Self-Immobilisation Enzyme
BMC Biotechnology BioMed Central Research article Open Access Spherezymes: A novel structured self-immobilisation enzyme technology Dean Brady*1, Justin Jordaan1, Clinton Simpson1, Avashnee Chetty2, Cherise Arumugam2 and Francis S Moolman2 Address: 1CSIR Biosciences, Ardeer Road, Modderfontein, 1645 South Africa and 2CSIR Materials Science and Manufacturing, Meiring Naudé Road, Brummeria, Pretoria, 0001 South Africa Email: Dean Brady* - [email protected]; Justin Jordaan - [email protected]; Clinton Simpson - [email protected]; Avashnee Chetty - [email protected]; Cherise Arumugam - [email protected]; Francis S Moolman - [email protected] * Corresponding author Published: 31 January 2008 Received: 8 May 2007 Accepted: 31 January 2008 BMC Biotechnology 2008, 8:8 doi:10.1186/1472-6750-8-8 This article is available from: http://www.biomedcentral.com/1472-6750/8/8 © 2008 Brady et al; licensee BioMed Central Ltd. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Abstract Background: Enzymes have found extensive and growing application in the field of chemical organic synthesis and resolution of chiral intermediates. In order to stabilise the enzymes and to facilitate their recovery and recycle, they are frequently immobilised. However, immobilisation onto solid supports greatly reduces the volumetric and specific activity of the biocatalysts. An alternative is to form self-immobilised enzyme particles. Results: Through addition of protein cross-linking agents to a water-in-oil emulsion of an aqueous enzyme solution, structured self-immobilised spherical enzyme particles of Pseudomonas fluorescens lipase were formed. -
Asymmetric Synthesis
Chapter 45 — Asymmetric synthesis - Pure enantiomers from Nature: the chiral pool and chiral induction - Asymmetric synthesis: chiral auxiliaries Enolate alkylation Aldol reaction - Enantiomeric excess (ee) - Asymmetric synthesis: chiral reagents and catalysts CBS reagent for chiral reductions Sharpless asymmetric epoxidation Synthesizing pure enantiomers starting from Nature’s chiral pool AcO OH HO B O O HO – O O HO + O N OH H3N OH HO OH O H … AcO HO OH O OH Sulcatol - insect pheremone HO Synthesis from the chiral pool — chiral induction turns one stereocenter into many 40 steps Me HO H Me H O O OH O O OBn O * * Only one H O HO chiral reagent H H Me OBn Me Deoxyribose Fragment of Brevetoxin B Asymmetric synthesis 1. Producing a new stereogenic centre on an achiral molecule makes two enantiomeric transition states of equal energy… and therefore two enantiomeric products in equal amounts. O O 1 1 Nu R R2 R R2 Nu E OH OH 1 O 1 Nu R R Nu R2 R2 1 R R2 O Ph OH HO Ph PhLi + N N N Asymmetric synthesis 2. O 1 R R* Nu When there is an existing O chiral centre, the two possible TS’s are diastereomeric and E 1 Nu R R* can be of different energy. Thus one isomer of the new stereogenic centre can be OH O OH produced in a larger amount. 1 1 R Nu Nu R *R 1 R* R R* HO Ph O O O Ph OH PhLi PhLi Ph Ph N N N N N Ph N N N N N OH Ph O O O Ph OH Ph A removable chiral centre… synthesis with chiral auxiliaries O ??? O R R 1) Add a chiral 3) Remove the auxiliary chiral auxiliary O O R* R* 2) Add the new stereocentre via chiral induction Enantiopure oxazolidinones as chiral auxiliaries 1. -
A Sustainable, Two-Enzyme, One-Pot Procedure
A Sustainable, Two-Enzyme, One-Pot Procedure for the Synthesis of Enantiomerically Pure α-Hydroxy Acids Andrzej Chmura Cover picture: Manihot esculenta (cassava), source: http://www.hear.org/starr/images/image/?q=090618-1234&o=plants SEM photograph of an Me HnL CLEA (author: Dr. Rob Schoevaart, CLEA Technologies, Delft, The Netherlands) Cover design by Andrzej Chmura A Sustainable, Two-Enzyme, One-Pot Procedure for the Synthesis of Enantiomerically Pure α-Hydroxy Acids PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Technische Universiteit Delft, op gezag van de Rector Magnificus prof.ir. K.C.A.M. Luyben, voorzitter van het College voor Promoties, in het openbaar te verdedigen op dinsdag 7 december 2010 om 12.30 uur door Andrzej CHMURA Magister inŜynier in Chemical Technology, Politechnika Wrocławska, Wrocław, Polen en Ingenieur in Chemistry, Hogeschool Zeeland, Vlissingen, Nederland geboren te Łańcut, Polen Dit proefschrift is goedgekeurd door de promotor: Prof. dr. R.A. Sheldon Copromotor: Dr. ir. F. van Rantwijk Samenstelling promotiecommissie: Rector Magnificus Voorzitter Prof. dr. R.A. Sheldon Technische Universiteit Delft, promotor Dr. ir. F. van Rantwijk Technische Universiteit Delft, copromotor Prof. dr. I.W.C.E. Arends Technische Universiteit Delft Prof. dr. W.R. Hagen Technische Universiteit Delft em. Prof. dr. A.P.G. Kieboom Universiteit Leiden Prof. dr. A. Stolz Universität Stuttgart Prof. dr. V. Švedas Lomonosov Moscow State University Prof. dr. J.J. Heijnen Technische Universiteit Delft, reserve lid The research described in this thesis was financially supported by The Netherlands Research Council NWO under the CERC3 programme and by COST action D25. ISBN/EAN: 978-90-9025856-0 Copyright © 2010 by Andrzej Chmura All rights reserved. -
Stereoselective Synthesis of Chiral
S S symmetry Article Stereoselective Synthesis of Chiral α-SCF3-β-Ketoesters FeaturingArticle a Quaternary Stereocenter Stereoselective Synthesis of Chiral α-SCF3-β-Ketoesters Monica Fiorenza Boselli, Chiara Faverio, Elisabetta Massolo, Laura Raimondi, Alessandra Puglisi andFeaturing Maurizio Benaglia a Quaternary * Stereocenter Monica Fiorenza Boselli, ChiaraDipartimento Faverio, diElisabetta Chimica, UniversitMassolo,à Lauradegli Studi Raimondi, di Milano, Alessandra Via Golgi 19,Puglisi I-20133 and Milano, Maurizio Italy; Benaglia * monicafi[email protected] (M.F.B.); [email protected] (C.F.); [email protected] (E.M.); [email protected] (L.R.); [email protected] (A.P.) *DipartimentoCorrespondence: di Chimica, [email protected]; Università degli Studi di Milano, Tel.: Via +39-02-5031-4171; Golgi 19, I-20133 Milano, Fax: +39-02-5031-4159 Italy; [email protected] (M.F.B.); [email protected] (C.F.); [email protected] (E.M.); Abstract:[email protected] development (L.R.); of [email protected] new and efficient methods, (A.P.) reagents, and catalysts for the introduction * Correspondence: [email protected]; Tel.: +39-02-5031-4171; Fax: +39-02-5031-4159 of fluorine atoms or fluorinated moieties in molecular scaffolds has become a topic of paramount importanceAbstract: The in development organic synthesis. of new and In thisefficient framework, methods, thereagents, incorporation and catalysts of thefor SCFthe introduc-3 group into organic moleculetion of fluorine has oftenatoms ledor fluorinated to beneficial moieties effects in molecular on the drug’s scaffolds metabolic has become stability a topic andof para- bioavailability. Heremount we importance report ourin organic studies synthesis.