Glycamine formation via reductive amination of oligosaccharides with benzylamine: efficient coupling of oligosaccharides to protein

Tomoaki Yoshida, Yuan Chuan Lee

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

The conventional reagents for the reductive amination of sugars, ammonium salts or ammonia, require relatively harsh conditions such as high temperatures or high concentrations. In addition, they give substantial amounts of dimeric byproducts. We have developed a method of using benzylamine as a donor to achieve near quantitative amination of reducing oligosaccharides. Benzylamine reacts with reducing oligosaccharides faster and yields less dimeric byproduct than ammonium ion, rendering it especially advantageous for preparative operation. In combination with a heterobifunctional reagent, 5-[N-(2,2-dimethoxyethyl)carbamoyl]pentanoyl azide, [Lee et al. Biochemistry, 28 (1989) 1856-1861], we could couple a nearly maximal number of phosphorylated mannopentaose molecules to ribonuclease A via its primary amino groups.

Original languageEnglish
Pages (from-to)175-186
Number of pages12
JournalCarbohydrate Research
Volume251
Issue numberC
DOIs
Publication statusPublished - 03-01-1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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