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Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids
[Image: see text] Enantiomerically pure tailor-made amino acids are in extremely high demand in nearly every sector of the health-related industries. In particular, the rapidly growing number of amino-acid-based pharmaceuticals calls for the development of advanced synthetic approaches featuring pra...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868592/ https://www.ncbi.nlm.nih.gov/pubmed/31763515 http://dx.doi.org/10.1021/acsomega.9b02940 |
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author | Han, Jianlin Romoff, Todd T. Moriwaki, Hiroki Konno, Hiroyuki Soloshonok, Vadim A. |
author_facet | Han, Jianlin Romoff, Todd T. Moriwaki, Hiroki Konno, Hiroyuki Soloshonok, Vadim A. |
author_sort | Han, Jianlin |
collection | PubMed |
description | [Image: see text] Enantiomerically pure tailor-made amino acids are in extremely high demand in nearly every sector of the health-related industries. In particular, the rapidly growing number of amino-acid-based pharmaceuticals calls for the development of advanced synthetic approaches featuring practicality and commercial viability. Here we provide a brief summary of the development of axially chiral tridentate Hamari ligands and their application for general asymmetric synthesis of various structural types of amino acids. The methodological diversity includes: dynamic kinetic resolution and (S)-/(R)-interconversion of unprotected amino acids and homologation of nucleophilic glycine equivalents via alkyl halide alkylation reactions as well as multiple-step transformations allowing preparation of polyfunctional and cyclic derivatives. The practicality of these methods is critically discussed. |
format | Online Article Text |
id | pubmed-6868592 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-68685922019-11-22 Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids Han, Jianlin Romoff, Todd T. Moriwaki, Hiroki Konno, Hiroyuki Soloshonok, Vadim A. ACS Omega [Image: see text] Enantiomerically pure tailor-made amino acids are in extremely high demand in nearly every sector of the health-related industries. In particular, the rapidly growing number of amino-acid-based pharmaceuticals calls for the development of advanced synthetic approaches featuring practicality and commercial viability. Here we provide a brief summary of the development of axially chiral tridentate Hamari ligands and their application for general asymmetric synthesis of various structural types of amino acids. The methodological diversity includes: dynamic kinetic resolution and (S)-/(R)-interconversion of unprotected amino acids and homologation of nucleophilic glycine equivalents via alkyl halide alkylation reactions as well as multiple-step transformations allowing preparation of polyfunctional and cyclic derivatives. The practicality of these methods is critically discussed. American Chemical Society 2019-11-07 /pmc/articles/PMC6868592/ /pubmed/31763515 http://dx.doi.org/10.1021/acsomega.9b02940 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Han, Jianlin Romoff, Todd T. Moriwaki, Hiroki Konno, Hiroyuki Soloshonok, Vadim A. Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids |
title | Development of Hamari Ligands for Practical Asymmetric
Synthesis of Tailor-Made Amino Acids |
title_full | Development of Hamari Ligands for Practical Asymmetric
Synthesis of Tailor-Made Amino Acids |
title_fullStr | Development of Hamari Ligands for Practical Asymmetric
Synthesis of Tailor-Made Amino Acids |
title_full_unstemmed | Development of Hamari Ligands for Practical Asymmetric
Synthesis of Tailor-Made Amino Acids |
title_short | Development of Hamari Ligands for Practical Asymmetric
Synthesis of Tailor-Made Amino Acids |
title_sort | development of hamari ligands for practical asymmetric
synthesis of tailor-made amino acids |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868592/ https://www.ncbi.nlm.nih.gov/pubmed/31763515 http://dx.doi.org/10.1021/acsomega.9b02940 |
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