Rapid catalyst-free hydrazone ligation: Protein-pyridoxal phosphoramides

Xiaojian Wang, James W. Canary

Research output: Contribution to journalArticlepeer-review

Abstract

Pyridoxal-5′-phosphate (PLP) represents an active form of Vitamin B6 that shows relatively fast imine formation with hydrazines under physiological conditions without the need of a catalyst. A convenient phosphate/amine conjugation protocol was developed to covalently link PLP to proteins, affording proteins capable of hydrazone formation with bioorthogonal hydrazinyl functional groups. Thus, the lectin Concanavalin A (Con A) was labeled with PLP. Pretreatment with fluorescein hydrazide gave dye-labeled Con A that labeled cell surfaces efficiently. Alternatively, pretargeting was achieved by labeling cells with Con A-PLP, then treatment in vitro with Alexa Fluor 488 hydrazide.

Original languageEnglish (US)
Pages (from-to)2329-2334
Number of pages6
JournalBioconjugate Chemistry
Volume23
Issue number12
DOIs
StatePublished - Dec 19 2012

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

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