Investigations of the Substrate Specificity of Lacticin 481 Synthetase and Utilization in Peptide Engineering Applications
Levengood, Matthew
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https://hdl.handle.net/2142/84328
Description
Title
Investigations of the Substrate Specificity of Lacticin 481 Synthetase and Utilization in Peptide Engineering Applications
Author(s)
Levengood, Matthew
Issue Date
2008
Doctoral Committee Chair(s)
van der Donk, Wilfred A.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Biochemistry
Language
eng
Abstract
The promiscuous activity of LctM toward LctA prepeptides containing nonproteinogenic amino acids prompted the evaluation of LctM as a general catalyst for the introduction of post-translational modifications in non-lantibiotic peptides fused to the LctA leader peptide. LctM was utilized to efficiently introduce dehydrated, phosphorylated, and lanthionine cross-linked amino acids into therapeutically relevant non-lantibiotic peptides. Furthermore, enzymatically installed dehydro amino acids were used as sites of ligation with a variety of thiol nucleophiles for the preparation of peptide conjugates. Lastly, the role of the leader peptide in lacticin 481 biosynthesis was investigated. Surprisingly, the leader peptide was not required for dehydration activity of LctM, although it greatly enhanced the catalytic efficiency of LctM.
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