Synthesis, Characterization, and Application of Iodoacetamide Derivatives Utilized for the ALiPHAT Strategy

Hydrophobic tags, derived from iodoacetamide, were synthesized, characterized, and utilized to alkylate peptide E-76, a known inhibitor of coagulation factor VIIIa, and two other cysteine containing peptides. The electrospray response of each tagged peptide was compared against the same peptide alky...

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Veröffentlicht in:	Journal of the American Chemical Society 2008-02, Vol.130 (7), p.2122-2123
Hauptverfasser:	Williams, D. Keith, Meadows, Corey W, Bori, Ibrahim D, Hawkridge, Adam M, Comins, Daniel L, Muddiman, David C
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Amino Acid Sequence Cysteine - chemistry Factor VIIIa - antagonists & inhibitors Hydrophobic and Hydrophilic Interactions Iodoacetamide - analogs & derivatives Iodoacetamide - chemical synthesis Iodoacetamide - chemistry Molecular Sequence Data Peptides - analysis Peptides - chemistry Spectrometry, Mass, Electrospray Ionization - methods
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Beschreibung
Zusammenfassung:	Hydrophobic tags, derived from iodoacetamide, were synthesized, characterized, and utilized to alkylate peptide E-76, a known inhibitor of coagulation factor VIIIa, and two other cysteine containing peptides. The electrospray response of each tagged peptide was compared against the same peptide alkylated with iodoacetamide. E-76 peptide alkylated with the synthesized tags demonstrated an increase in electrospray response of up to 429 times when compared to that alkylated with iodoacetamide.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja076849y