Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester
| Autor: | Mami Shikanai, Kento Hayashi, Natsumi Kurokawa, Makoto Hashimoto, Haruka Ikemoto, Kazuhiro Oida, Yasuyuki Hashidoko, Yasuko Sakihama, Fumina Ohashi, Zetryana Puteri Tachrim |
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| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Acylation
Succinimides Pharmaceutical Science α-amino aryl-ketone Chemistry Techniques Synthetic 010402 general chemistry 01 natural sciences Article Friedel-Crafts acylation Analytical Chemistry lcsh:QD241-441 lcsh:Organic chemistry Drug Discovery Peptide bond Organic chemistry Amino Acids Physical and Theoretical Chemistry Enantiomeric excess Friedel–Crafts reaction Racemization chemistry.chemical_classification Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Diastereomer α-amino acid Esters N-hydroxysuccinimide ester Friedel–Crafts acylation racemization Ketones 0104 chemical sciences Amino acid alpha-amino aryl-ketone Chemistry (miscellaneous) Molecular Medicine alpha-amino acid Chirality (chemistry) |
| Zdroj: | Molecules, Vol 22, Iss 10, p 1748 (2017) Molecules; Volume 22; Issue 10; Pages: 1748 Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry |
| ISSN: | 1420-3049 |
| Popis: | Chiral N-protected alpha-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 alpha-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 alpha-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 alpha-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 alpha-amino aryl-ketone without loss of optical purity. |
| Databáze: | OpenAIRE |
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