Extensive modification of protein amino groups by reductive addition of different sized substituents

International Journal of Peptide and Protein Research
K FretheimR E Feeney

Abstract

The amino groups of ovomucoid, lysozyme and ovotransferrin have been extensively alkylated by reacting the proteins with various carbonyl reagents in the presence of sodim borohydride. The extent of modification ranged from 40 to 100%. Essentially monosubstitution was obtained with acetone, cyclopentanone, cyclohexanone and benzaldehyde, while 20--50% disubstitution was obtained with N-butanal and nearby 100% disubstitution was obtained with formaldehyde. Both the methylated and isopropylated derivatives of all three proteins were soluble and retained almost full biochemical activities, but introduction of the larger substituents caused precipitation with lysozyme and ovotransferrin.

References

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Citations

Nov 1, 1991·International Journal of Peptide and Protein Research·Y Fujita, Y Noda
Jun 1, 1985·International Journal of Peptide and Protein Research·K FretheimO Harbitz
Aug 1, 1992·International Journal of Peptide and Protein Research·Y Fujita, Y Noda
Jul 1, 1985·International Journal of Peptide and Protein Research·W S WongR E Feeney
Mar 1, 1981·International Journal of Peptide and Protein Research·K F GeogheganR E Feeney
Jun 29, 1988·Journal of Chromatography·E M BrownR Greenberg
Jun 26, 1981·Biochimica Et Biophysica Acta·R L KarpelM D Delahunty
Nov 17, 2001·Biomacromolecules·G LevesqueT N Pham
May 8, 2009·Journal of the American Society for Mass Spectrometry·Jianjun ZhaiHaining Zhu

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