Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan

Ryo Ota, Yumi Okamoto, Christopher J. Vavricka, Takuji Oka, Emiko Matsunaga, Kaoru Takegawa, Hiromasa Kiyota, Minoru Izumi

Research output: Contribution to journalArticle

Abstract

β-D-Galactofuranose (Galf) is a component of polysaccharides and glycoconjugates. There are few reports about the involvement of galactofuranosyltransferases and galactofuranosidases (Galf-ases) in the synthesis and degradation of galactofuranose-containing glycans. The cell walls of filamentous fungi in the genus Aspergillus include galactofuranose-containing polysaccharides and glycoconjugates, such as O-glycans, N-glycans, and fungal-type galactomannan, which are important for cell wall integrity. In this study, we investigated the synthesis of p-nitrophenyl β-D-galactofuranoside and its disaccharides by chemo-enzymatic methods including use of galactosidase. The key step was selective removal of the concomitant pyranoside by enzymatic hydrolysis to purify p-nitrophenyl β-D-galactofuranoside, a promising substrate for β-D-galactofuranosidase from Streptomyces species.

Original languageEnglish
Pages (from-to)99-103
Number of pages5
JournalCarbohydrate Research
Volume473
DOIs
Publication statusPublished - Feb 1 2019

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Disaccharides
Aspergillus
Polysaccharides
Glycoconjugates
Cell Wall
Cells
Galactosidases
Enzymatic hydrolysis
Streptomyces
Fungi
Hydrolysis
galactomannan
Degradation
Substrates

Keywords

  • Chemo-enzymatic synthesis
  • Galactofuranose
  • Galactosidase
  • p-Nitrophenyl galactofuranoside

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan. / Ota, Ryo; Okamoto, Yumi; Vavricka, Christopher J.; Oka, Takuji; Matsunaga, Emiko; Takegawa, Kaoru; Kiyota, Hiromasa; Izumi, Minoru.

In: Carbohydrate Research, Vol. 473, 01.02.2019, p. 99-103.

Research output: Contribution to journalArticle

Ota, Ryo ; Okamoto, Yumi ; Vavricka, Christopher J. ; Oka, Takuji ; Matsunaga, Emiko ; Takegawa, Kaoru ; Kiyota, Hiromasa ; Izumi, Minoru. / Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan. In: Carbohydrate Research. 2019 ; Vol. 473. pp. 99-103.
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