Synlett 2022; 33(07): 669-673
DOI: 10.1055/a-1754-2437
letter

Outside-In Strategy for Peptide-Based Methacrylate and Methacrylamide Zwitterionic Cross-Linkers

Moubani Chakraborty
,
Kristopher V. Waynant
University of Idaho Start-Up Funds


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Abstract

Polyampholyte hydrogels have shown promise as functional biomaterial platforms with resistance to nonspecific protein adsorption (nonbiofouling). Yet there are few zwitterionic cross-linkers available to complement these materials and to provide an extended charge density throughout the 3D network. The recent development of peptide-based zwitterionic cross-linkers has shown merit. Indeed, the use of functionalizable amino acids permits the synthesis of a series of peptide-based zwitterionic methacrylate and methacrylamide cross-linkers. Methacrylate additions prior to peptide coupling provide an outside-in strategy when using natural l-serine or l-lysine as substrates to produce a series of methacrylate and methacrylamide combinations, expanding the library of peptide-based cross-linkers. Here, we describe the preparation of such dipeptide combinations as Ser-Lys, Lys-Ser, and Lys-Lys in zwitterionic bis(methacrylate/methacrylamide) cross-linkers. To highlight the utility of this method and its potential to increase the distance between zwitterionic components, syntheses of the tripeptide Lys-Gly-Lys dimethacrylamide and Ser-Gly-Ser dimethacrylate are reported.

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Publication History

Received: 24 November 2021

Accepted after revision: 28 January 2022

Accepted Manuscript online:
28 January 2022

Article published online:
21 February 2022

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