Synthesis of Diphenylalanine-based Peptide Aldehydes and their Self-Assembly Propensity in a Dynamic Combinatorial Library Open Access

Zhang, Yusheng (2015)

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Small peptides with the ability to self-assemble have been investigated both for novel biomaterial discovery purposes and for origins of life research. Diphenylalanine is an example of a small peptide that have been thoroughly studied, and it has been shown to exhibit diverse self-assembly capabilities. Furthermore, chemical modifications that allow each peptide monomer to dynamically link with one another gives the peptide systems even greater possibility to form diverse structures. Inspired by previous studies in the Lynn Lab, this paper discloses the synthesis of diphenylalanine-based peptide aldehydes and discusses the various attributes of the dynamic combinatorial library (DCL) established using the diphenylalanine based peptide aldehydes.

Table of Contents

Introductions 8

Part 1: Synthesizing the Peptides

I. Coupling Amino Acids 15

II. Efforts in procuring Homoserine 17

III. Synthesis, purification, and protection of peptide aldehydes 20

IV. Fmoc removal and further purifications 23

Part 2: Establishing and Characterizing the DCL 25

Conclusion 33

References 35

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