Requirement for a different hydrophobic moiety and reliable chromogenic substrate for endo-type glycosylceramidases

Yoshiaki Miura, Tsutomu Arai, Atsuko Ohtake, Makoto Ito, Kenji Yamamoto, Tatsuya Yamagata

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A series of synthetic lactosides with aglycones that differed in length and structure were used to determine the substrate specificity of endo-type glycosylceramidases. Endoglycoceramidases (EGCase) from bacteria preferred lactosides with an acylamide structure over simple n-alkyl lactosides. While ceramide glycanase (CGase) from leech did not show preference, N-Acylaminoethyl β-lactosides and n-alkyl lactosides were substrates for both EGCase and CGase, but N-acylaminobutyl β-lactosides, whose acylamide residue differs from that in ceramide, were not hydrolyzed by EGCases. Thus, EGCases, but not CGase, appear to require an N-acyl group at the same position as that of intact glycosphingolipid for substrate recognition. A p-nitrophenyl lactoside derivative possessing an N-acyl chain was degraded by both EGCases and CGase and this chromogenic substrate may be an alternative substrate for endo-type glycosylceramidase activity. K(m) of the chromogenic lactoside for CGase and Rhodococcus EGCase were 28 μM and 2.9 mM, respectively.

Original languageEnglish
Pages (from-to)957-960
Number of pages4
JournalGlycobiology
Volume9
Issue number9
DOIs
Publication statusPublished - Sep 1 1999

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Lactase-Phlorizin Hydrolase
Chromogenic Compounds
endoglycoceramidase
Substrates
Chromogenics
Glycosphingolipids
Rhodococcus
Ceramides
Leeches
lactosides
Substrate Specificity
Bacteria
ceramide glycanase
Derivatives

All Science Journal Classification (ASJC) codes

  • Biochemistry

Cite this

Requirement for a different hydrophobic moiety and reliable chromogenic substrate for endo-type glycosylceramidases. / Miura, Yoshiaki; Arai, Tsutomu; Ohtake, Atsuko; Ito, Makoto; Yamamoto, Kenji; Yamagata, Tatsuya.

In: Glycobiology, Vol. 9, No. 9, 01.09.1999, p. 957-960.

Research output: Contribution to journalArticle

Miura, Yoshiaki ; Arai, Tsutomu ; Ohtake, Atsuko ; Ito, Makoto ; Yamamoto, Kenji ; Yamagata, Tatsuya. / Requirement for a different hydrophobic moiety and reliable chromogenic substrate for endo-type glycosylceramidases. In: Glycobiology. 1999 ; Vol. 9, No. 9. pp. 957-960.
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