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Journal of Biosciences

, Volume 16, Issue 3, pp 127–135 | Cite as

Diketopinic acid — A novel reagent for the modification of arginine

  • C. S. Pande
  • D. Bassi
  • Neena Jain
  • A. Dhar
  • J. D. Glass
Article

Abstract

Diketopinic acid has been synthesized and shown to be a reagent of choice for specific, reversible modification of the guanidine groups of arginine residues. Diketopinic acid is a yellow crystalline substance and the carboxyl group of the reagent is a convenient handle for attachment to other molecules. The adducts of diketopinoyl derivatives with the guanidine group are cleaved by 0.2 M o-phenylenediamine at pH 8–9. The modification and regeneration of arginine and of arginyl residues in soyabean trypsin inhibitor and insulin are presented as demonstrations of the use of the reagent. The use of diketopinoyl resin in the separation of oxidized A and B chains of insulin has been discussed.

Keywords

Diketone reversible modification of arginine residues aminopolymer diketopolymer 

Abbreviations Used

DKPA

Diketopinic acid (2,3-diketo-10-bornanoic acid)

STI

soyabean trypsin inhibitor

DMF

dimethylformamide

DCHA

dicyclohexylamine

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References

  1. Pande C S, Pelzig M and Glass J D 1980 Camphorquinone-10-sulfonic acid and derivatives, convenient reagents for reversible modification of arginine residues;Proc, Natl. Acad. Sci. USA 77 895–899Google Scholar
  2. Sutherland H and Shriner R L 1936 Anamalous mutarolation of salts of Reychler acid IV;J. Am. Chem. Soc. 58 62–63CrossRefGoogle Scholar
  3. Bartlett P D and Knox L H 1939 Bicyclic structures prohibiting the Walden inversion;J. Am. Chem. Soc. 61 3184–3192CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 1991

Authors and Affiliations

  • C. S. Pande
    • 1
  • D. Bassi
    • 1
    • 2
  • Neena Jain
    • 1
  • A. Dhar
    • 1
  • J. D. Glass
    • 1
    • 3
  1. 1.Department of ChemistryHimachal Pradesh UniversityShimlaIndia
  2. 2.IRSONGCChandkhera, AhmedabadIndia
  3. 3.Brookhaven National LaboratoryMedical Research CenterUptonUSA

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