Preparation of Photoreactive Derivatives of Glutathione and [9-(2-Mercaptotryptophan)]corticotropin by Selective Modification of the Sulfhydryl Group

Koji Muramoto, J. Ramachandran

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The photoreactive arylsulfenyl chlorides 2-nitro-4- azidophenylsulfenyl chloride (2,4-NAPS-Cl) and 2-nitro-5-azidophenylsulfenyl chloride (2,5-NAPS-Cl) have been used for the selective modification of thiol groups in glutathione and [Trp(SH)9]corticotropin (ACTH). Both reagents reacted rapidly with both types of thiol groups to form unsymmetrical disulfides. The photoreactive derivatives of glutathione and [Trp(SH)9]ACTH were stable to neutral and acidic conditions but were readily cleaved above pH 9 and by β-mercaptoethanol. Photolysis of the NAPS derivatives of [Trp(SH)9]-ACTH at neutral pH resulted in the formation of covalently linked polymers and dimers which yielded monomer upon treatment with β-mercaptoethanol. Analysis of the amino acid composition of acid hydrolysates of photolyzed monomeric and dimeric products indicated a decrease in proline, valine, tyrosine, and phenylalanine.

Original languageEnglish
Pages (from-to)3376-3380
Number of pages5
JournalBiochemistry
Volume20
Issue number12
DOIs
Publication statusPublished - 1981 Jun
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry

Fingerprint

Dive into the research topics of 'Preparation of Photoreactive Derivatives of Glutathione and [9-(2-Mercaptotryptophan)]corticotropin by Selective Modification of the Sulfhydryl Group'. Together they form a unique fingerprint.

Cite this