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van der Donk, Wilfred A. Zhu, Yantao 2015-09-25T22:13:02Z 2015-09-25T22:13:02Z 10000-01-01 2003 2003 Beyond its utility in the preparation of lantibiotics, this method is also well suited for the preparation of peptide conjugates. The functionalities encountered in natural amino acids include nucleophilic, acidic, and basic groups, but no electrophilic moieties. Thus, introduction of an electrophilic group into peptides will provide a handle for the chemoselective incorporation of nucleophiles. Based on this analysis, a convergent route involving site-specific modification of the unprotected dehydropeptide (the electrophilic handle) by Michael additions of suitable nucleophiles was developed. The C-terminal sequence of N-Ras, a number of other lipid peptides and S-linked glycopeptides were prepared through the Michael addition of corresponding thiolates to dehydropeptides. Furthermore, the preparation of dehydropeptides and the Michael addition were also illustrated to be compatible with solid phase. Made available in DSpace on 2015-09-25T22:13:02Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 3102013.pdf: 7588509 bytes, checksum: aa9dc6bfc88d33032cc503892d5755ba (MD5) Previous issue date: 2003 Embargo set by: Seth Robbins for item 85404 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 163 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2003. http://hdl.handle.net/2142/84123 (MiAaPQ)AAI3102013 eng Chemistry, Organic Preparation of Dehydropeptides and Their Application in the Convergent Synthesis of Peptide Conjugates text Ph.D. Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation