64191-05-5Relevant academic research and scientific papers
Synthesis of N-Maleoyl-aminoacids and -peptides
Augustin, Manfred,Mueller, Wolfgang
, p. 789 - 798 (2007/10/02)
N-Maleoyl-aminoacid-N'-hydroxysuccinimidesters 3 or N-maleoyl-aminobenzoic acids 5 are synthsized from N-maleyl-aminoacids 1 on different ways.N-maleoyl-aminobenzoic-4-nirophenyl-, -2-nitro-phenyl- or 2,4-dinitro-phenylesters 6, 7 and 8 will be obtained from 1 or 5. o-Mercaptoaniline, thiourea or cysteine react with 5 to benzothiazines 9, thiazolidines 10 and 1,4-thiazines 11.From 5 the peptides 12 are yielded.The pentapeptide 13 are formed from 12 by addition of glutathione.
Preparation and Characterization of Hetero-bifunctional Cross-linking Reagents for Protein Modifications
Kitagawa, Tsunehiro,Shimozono, Takuro,Aikawa, Tadaomi,Yoshida, Toyokichi,Nishimura, Haruki
, p. 1130 - 1135 (2007/10/02)
Ten aromatic and aliphatic cross-linking reagents of hetero-bifunctional type were synthesized as part of a search for useful reagents of this type.All of the reagents possess two selectively reactive groups a maleimide group which can combine with a thiol group via its double bond and an N-Hydroxysuccinimidyl ester (one of the most hydrophilic active esters), which can react with an ammmine group.It was found that the active esters of the reagents tested were mostly more reactive with lysine than with leucine, and acylated amino acids more rapidly at pH 8.0 than at pH 7.0.It was also found that the stability of the maleimide group in the compounds tested depends largely upon the pH of the buffer used.The most stable pH was 5.0-6.0.To use one of the present compounds as a cross-linker, the crystalline reagent should be dissolved in tetrahydrofuran of dioxane and the solution used for cross-linking.The acylation step should be carried out first with thiol addition to the maleimide group as the second step.The optimum pH of the buffer used for the first step is slightly basic.The reaction time should be limited to less than 1 hr.When the first step is over, the pH of the reaction mixture should be changed to 5.0-6.0.Keywords---cross-linker; hetero-bifunctional reagent; reactivity of N-hydroxy-succinimidyl ester; stability of maleimide residue; N-(maleimidobenzoyloxy)succinimide derivative; N-(maleimidoalkyloxy)succinimide derivative
