Synthesis of β-Peptide Standards for Use in Model Prebiotic Reactions
A one-pot method was developed for the preparation of a series of β-alanine standards of moderate size (2 to ≥12 residues) for studies concerning the prebiotic origins of peptides. The one-pot synthesis involved two sequential reactions: (1) dry-down self-condensation of β-alanine methyl ester, yielding β-alanine peptide methyl ester oligomers, and (2) subsequent hydrolysis of β-alanine peptide methyl ester oligomers, producing a series of β-alanine peptide standards. These standards were then spiked into a model prebiotic product mixture to confirm by HPLC the formation of β-alanine peptides under plausible reaction conditions. The simplicity of this approach suggests it can be used to prepare a variety of β-peptide standards for investigating differences between α- and β-peptides in the context of prebiotic chemistry.
KeywordsOrigins of life Prebiotic β-peptide β-amino acid β-alanine β-alanine methyl ester Oligomerization
The authors thank Esther Varon for technical assistance and manuscript reviewers for beneficial comments. This work was supported by NSF and the NASA Astrobiology Program under the NSF Center for Chemical Evolution (CHE-1504217) as well as the College of Charleston (Summer Undergraduate Research Fellowship to SLE; start-up funds to JGF).
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