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Synfacts 2015; 11(5): 0555
DOI: 10.1055/s-0034-1380672
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Supported Library-Based Screening of Peptide Catalysts

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Heeyoel Baek
Akagawa K, Sakai N, Kudo K * University of Tokyo, Japan
Histidine-Containing Peptide Catalysts Developed by a Facile Library Screening Method.

Angew. Chem. Int. Ed. 2015;
54: 1822-1826
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Further Information

Publication History

Publication Date:
17 April 2015 (online)

 
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Key words

Michael addition - peptides - α,β-unsaturated aldehydes - heterogeneous catalysis

Significance

A resin-supported peptide 1 [Pro-d-Pro-Aib-Try-His-(Leu-Leu-Aib)2-TentaGel] was identified as an efficient peptide catalyst for the Michael addition of malonates to α,β-unsaturated aldehydes via a combinatorial approach using a resin-supported peptide library. Thus, the reaction of para-nitrocinnamaldehyde with the dye-anchored malonate was carried out with a resin-­supported peptide library (100 members) during which a CHO group of the resulting Michael adduct condensed with the terminal prolyl unit of the library in situ. Through this screening protocol, a resin bead bearing a more catalytically active peptide was stained more strongly.


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Comment

A resin-supported peptide 1 catalyzed the Michael reaction of dialkyl malonates and an α,β-unsaturated aldehydes to afford the corresponding products in up to 89% yield with up to 98% ee. The catalytic activity of 1 in which a histidine moiety was equipped at the fifth position was superior to that of [Pro-d-Pro-Aib-His-Phe-(Leu-Leu-Aib)]2 and [Pro-d-Pro-Aib-Phe-His-(Leu-Leu-Aib)]2. The authors indicated that the histidine moiety plays a critical role for accelerating the ­reaction by capturing the substrate.


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