PMID: 2997056Jul 1, 1985Paper

1-Deoxyglycitolation of protein amino groups and their regeneration by periodate oxidation

International Journal of Peptide and Protein Research
W S WongR E Feeney

Abstract

Reductive alkylation of lysyl epsilon-amino groups with sugars (1-deoxyglycitolation) using pyridine borane as the reducing agent has been recently described [Wong, W.S.D., Osuga, D.T. & Feeney, R.E. (1984) Anal. Biochem. 139, 58-67]. The regeneration of the lysines has now been achieved by oxidation with approximately 10 mM periodate. In experiments with glycitolated bovine serum albumin, reactions using 5, 20, and 80 mM periodate were essentially complete in the first 10 min. Oxidations of methionine to the sulfoxide were evident even at this lower concentration of periodate, while higher concentrations and prolonged reaction times only caused unnecessary destruction of amino acids. The removal was shown to occur in a wide pH range with little variation in the recovery of the lysines. The degree of glycitolation, or the nature of the attached carbohydrate residues, had no effect on the yield of products. Reductive 1-deoxygalactitolation of approximately 55% of the lysyl epsilon-amino groups of lysozyme caused no loss in enzymatic activity; when 5 mM periodate was used to remove the 1-deoxygalactitol moiety, approximately 95% of the amino groups were regenerated, concomitant with destruction of approximately 16% of the activit...Continue Reading

References

Apr 15, 1977·European Journal of Biochemistry·M A Krysteva, I D Dobrev
Nov 27, 1979·Biochemistry·K F GeogheganR E Feeney
Jan 1, 1979·International Journal of Peptide and Protein Research·K FretheimR E Feeney
Feb 10, 1976·Biochemistry·D WangS Moore
Aug 1, 1968·The Biochemical Journal·R Fields, H B Dixon
Nov 12, 1968·Biochimica Et Biophysica Acta·J GanC H Li
Oct 1, 1982·Analytical Biochemistry·R B YamasakiR E Feeney
May 15, 1984·Analytical Biochemistry·W S WongR E Feeney
Feb 1, 1953·Biochimica Et Biophysica Acta·A KATCHALSKY, N SHARON
Jan 1, 1965·The Biochemical Journal·J R CLAMP, L HOUGH

❮ Previous
Next ❯

Citations

Feb 1, 1987·International Journal of Peptide and Protein Research·R E Feeney

❮ Previous
Next ❯

Related Concepts

Related Feeds

Bacterial Cell Wall Structure

Bacterial cell walls are made of peptidoglycan (also called murein), which is made from polysaccharide chains cross-linked by unusual peptides containing D-amino acids. Here is the latest research on bacterial cell wall structures.

Bacterial Cell Wall Structure (ASM)

Bacterial cell walls are made of peptidoglycan (also called murein), which is made from polysaccharide chains cross-linked by unusual peptides containing D-amino acids. Here is the latest research on bacterial cell wall structures.