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Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester
Chiral N-protected α-amino aryl-ketones are one of the useful precursors used in the synthesis of various biologically active compounds and can be constructed via Friedel–Crafts acylation of N-protected α-amino acids. One of the drawbacks of this reaction is the utilization of toxic, corrosive and m...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151496/ https://www.ncbi.nlm.nih.gov/pubmed/29039791 http://dx.doi.org/10.3390/molecules22101748 |
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author | Tachrim, Zetryana Puteri Oida, Kazuhiro Ikemoto, Haruka Ohashi, Fumina Kurokawa, Natsumi Hayashi, Kento Shikanai, Mami Sakihama, Yasuko Hashidoko, Yasuyuki Hashimoto, Makoto |
author_facet | Tachrim, Zetryana Puteri Oida, Kazuhiro Ikemoto, Haruka Ohashi, Fumina Kurokawa, Natsumi Hayashi, Kento Shikanai, Mami Sakihama, Yasuko Hashidoko, Yasuyuki Hashimoto, Makoto |
author_sort | Tachrim, Zetryana Puteri |
collection | PubMed |
description | Chiral N-protected α-amino aryl-ketones are one of the useful precursors used in the synthesis of various biologically active compounds and can be constructed via Friedel–Crafts acylation of N-protected α-amino acids. One of the drawbacks of this reaction is the utilization of toxic, corrosive and moisture-sensitive acylating reagents. In peptide construction via amide bond formation, N-hydroxysuccinimide ester (OSu), which has high storage stability, can react rapidly with amino components and produces fewer side reactions, including racemization. This study reports the first synthesis and utilization of N-trifluoroacetyl (TFA)-protected α-amino acid-OSu as a potential acyl donor for Friedel–Crafts acylation into various arenes. The TFA-protected isoleucine derivative and its diastereomer TFA-protected allo-isoleucine derivative were investigated to check the retention of α-proton chirality in the Friedel–Crafts reaction. Further utilization of OSu in other branched-chain and unbranched-chain amino acids results in an adequate yield of TFA-protected α-amino aryl-ketone without loss of optical purity. |
format | Online Article Text |
id | pubmed-6151496 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61514962018-11-13 Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester Tachrim, Zetryana Puteri Oida, Kazuhiro Ikemoto, Haruka Ohashi, Fumina Kurokawa, Natsumi Hayashi, Kento Shikanai, Mami Sakihama, Yasuko Hashidoko, Yasuyuki Hashimoto, Makoto Molecules Article Chiral N-protected α-amino aryl-ketones are one of the useful precursors used in the synthesis of various biologically active compounds and can be constructed via Friedel–Crafts acylation of N-protected α-amino acids. One of the drawbacks of this reaction is the utilization of toxic, corrosive and moisture-sensitive acylating reagents. In peptide construction via amide bond formation, N-hydroxysuccinimide ester (OSu), which has high storage stability, can react rapidly with amino components and produces fewer side reactions, including racemization. This study reports the first synthesis and utilization of N-trifluoroacetyl (TFA)-protected α-amino acid-OSu as a potential acyl donor for Friedel–Crafts acylation into various arenes. The TFA-protected isoleucine derivative and its diastereomer TFA-protected allo-isoleucine derivative were investigated to check the retention of α-proton chirality in the Friedel–Crafts reaction. Further utilization of OSu in other branched-chain and unbranched-chain amino acids results in an adequate yield of TFA-protected α-amino aryl-ketone without loss of optical purity. MDPI 2017-10-17 /pmc/articles/PMC6151496/ /pubmed/29039791 http://dx.doi.org/10.3390/molecules22101748 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Tachrim, Zetryana Puteri Oida, Kazuhiro Ikemoto, Haruka Ohashi, Fumina Kurokawa, Natsumi Hayashi, Kento Shikanai, Mami Sakihama, Yasuko Hashidoko, Yasuyuki Hashimoto, Makoto Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester |
title | Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester |
title_full | Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester |
title_fullStr | Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester |
title_full_unstemmed | Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester |
title_short | Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester |
title_sort | synthesis of chiral tfa-protected α-amino aryl-ketone derivatives with friedel–crafts acylation of α-amino acid n-hydroxysuccinimide ester |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151496/ https://www.ncbi.nlm.nih.gov/pubmed/29039791 http://dx.doi.org/10.3390/molecules22101748 |
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