Date on Master's Thesis/Doctoral Dissertation
12-2003
Document Type
Master's Thesis
Degree Name
M.S.
Department
Chemistry
Committee Chair
Spatola, A. F.
Subject
Peptides--Synthesis
Abstract
Chapter 1 detailed the synthesis method of hydroxamate peptides derivatives of pentapeptide Ac-PHSXX\'-N-NH2 by solid phase hydroxamate peptide synthesis method. The glutamic acid/aspartic acid side chain was modified to hydroxamic acid by on resin N-C coupling. The hydroxamate benzyl protecting group was removed during HF cleavage. In Chapter 2 a novel multiple hydroxamic acid peptide siderophore was prepared and the metal binding activity of these peptides was studied by ESI-MS and MS/MS. Siderophore peptide Ac-Gly1-Glu2(NHOH)-D-Pro3-Gly4-Glu5(NHOH)-D-Pro6-NH2 was found to have significant preference to Fe(III) over Zn(II) and Ni(II), while the natural peptide analogue Ac-Gly1-Glu2-D-Pro 3-Gly4-Glu5-D-Pro6-NH2 did not show any obvious preference in these metal ions. The study of these multi hydroxamate ligands metal coordination revealed that the C-terminal binding site (Glu5(NHOH)) has the stronger chelation capability than the N terminal (Glu2(NHOH)) metal binding site and the amide bonds between glutamic acid and proline were identified as the most fragile bonds by MS/MS study.
Recommended Citation
Sun, Yingchuan Susan 1975-, "Synthesis of peptides with hydroxamic acid side chain appendages." (2003). Electronic Theses and Dissertations. Paper 1407.
https://doi.org/10.18297/etd/1407
