Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media

Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media

The resin-supported peptide catalyst having the terminal five-residue Pro-d-Pro-Aib-Trp-Trp combined with polyleucine successfully catalyzed the asymmetric α-oxyamination of aldehydes in aqueous media. The secondary structure and the chirality sense of the hydrophobic polyleucine chain significantly...

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Veröffentlicht in:Organic letters 2010-04, Vol.12 (8), p.1804-1807
Hauptverfasser: Akagawa, Kengo, Fujiwara, Takuma, Sakamoto, Seiji, Kudo, Kazuaki
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Amination
Amino Acid Sequence
Catalysis
Models, Molecular
Peptides - chemistry
Protein Structure, Secondary
Resins, Synthetic - chemistry
Water - chemistry
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Zusammenfassung:The resin-supported peptide catalyst having the terminal five-residue Pro-d-Pro-Aib-Trp-Trp combined with polyleucine successfully catalyzed the asymmetric α-oxyamination of aldehydes in aqueous media. The secondary structure and the chirality sense of the hydrophobic polyleucine chain significantly affected both reactivity and enantioselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100415h