PMID: 3651395Jun 16, 1987Paper

Dihydroxypropylation of amino groups of proteins: use of glyceraldehyde as a reversible agent for reductive alkylation

Biochemistry
A S Acharya, B N Manjula

Abstract

The mode of derivatization of amino groups of proteins by glyceraldehyde, an aldotriose, depends on the presence or absence of reducing agent. In the presence of sodium cyanoborohydride, the Schiff base adducts of the aldehyde with the amino groups are reduced, and dihydroxypropylation of amino groups takes place (reductive mode). The reductively glycated lysine residue, N epsilon-(2,3-dihydroxypropyl)lysine, is a substituted alpha-amino alcohol. This alpha-amino alcoholic function of the derivatized lysine should be susceptible to periodate oxidation, and this oxidation is anticipated to result in the regeneration of the lysine residue. This aspect has been now investigated. Indeed, on mild periodate oxidation (15 mM periodate, 15 min at room temperature) of dihydroxypropylated ribonuclease A, nearly 95% of its N epsilon-(2,3-dihydroxypropyl)lysine residues were regenerated to lysine residues. The removal of the dihydroxypropyl groups by periodate oxidation could be accomplished within a wide pH range with little variation in the recovery of lysines. The possible usefulness of this reversible chemical modification procedure in the primary structural studies of proteins was investigated with a tryptic peptide of dihydroxypropyl...Continue Reading

References

Nov 27, 1979·Biochemistry·K F GeogheganR E Feeney
Aug 1, 1968·The Biochemical Journal·R Fields, H B Dixon
Jun 1, 1968·Biochemistry·G E Means, R E Feeney
Oct 1, 1982·Analytical Biochemistry·R B YamasakiR E Feeney
Jun 1, 1983·Proceedings of the National Academy of Sciences of the United States of America·A S Acharya, J M Manning
Jan 1, 1972·Methods in Enzymology·M Z Atassi, A F Habeeb
Jan 1, 1972·Methods in Enzymology·M J Hunter, M L Ludwig

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Citations

Sep 8, 2011·Journal of the American Chemical Society·Anne M WagnerE James Petersson
Aug 1, 1990·Proceedings of the National Academy of Sciences of the United States of America·P J JohnsonM Müller
Oct 6, 2000·Journal of Colloid and Interface Science·P A Suci, G G Geesey

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