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2008•Journal of the American Chemical SocietyRequires access

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

D. Keith Williams, Corey W. Meadows, Ibrahim D. Bori, Adam M. Hawkridge, Daniel L. Comins, David C. Muddiman

Open publisher page 46 citations

Abstract

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.

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What this paper is about

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.

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Available abstract

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.

Key concepts: Iodoacetamide, Chemistry, Alkylation, Peptide, Cysteine, Peptide mapping, Electrospray, Biochemistry

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