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. 2019 Sep 9;9(48):28241-28247.
doi: 10.1039/c9ra05797h. eCollection 2019 Sep 3.

Synthesis of a 1,2- cis-indoxyl galactoside as a chromogenic glycosidase substrate

Sakuto Nagata  1 , Hirotaka Tomida  1 , Haruka Iwai-Hirose  1   2 , Hide-Nori Tanaka  2   3 , Hiromune Ando  2   3 , Akihiro Imamura  1   2 , Hideharu Ishida  1   2   3
Affiliations

Synthesis of a 1,2- cis-indoxyl galactoside as a chromogenic glycosidase substrate

Sakuto Nagata et al. RSC Adv. .

Abstract

A synthetically challenging 1,2-cis-indoxyl galactoside, X-α-galactoside, was first prepared in this study using a cyclic ketone indoxyl acceptor and a glycosyl trichloroacetimidate donor to produce an enol glycoside and a 4,6-O-di-tert-butylsilylene-protected galactosyl donor to complete the synthesis. The target compound shows enzyme activity in the presence of α-galactosidase.

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Conflict of interest statement

There are no conflicts of interest to declare.

Figures

Fig. 1
Fig. 1. Using indoxyl glycosides to detect glycosidase activity.
Fig. 2
Fig. 2. Examples of the successful formation of 1,2-trans-indoxyl glycosides via (A) under basic conditions and (B) under acidic conditions. TBAHS: tetrabutylammonium hydrogen sulfate; NIS: N-iodosuccinimide.
Fig. 3
Fig. 3. X-α-galactoside, the target molecule in this study. X = 5-bromo-4-chloro-3-indoxyl.
Scheme 1
Scheme 1. Glycosylation of indoxyl 7 using DTBS-protected Gal thioglycoside donor 11. Reagents and conditions: (a) DTBS(OTf)2, Py, r.t.; Ac2O, r.t., 97% (2 steps in one-pot fashion).
Scheme 2
Scheme 2. The successful conditions for the stereoselective glycosylation of cyclic ketone derivative 14 using Gal trichloroacetimidate donor 13 reported by Liu et al.
Scheme 3
Scheme 3. Global deprotection of fully protected X-α-Gal.
Fig. 4
Fig. 4. Monitoring of α-galactosidase activity using the synthesized X-α-Gal compound.
See this image and copyright information in PMC

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    1. For review see:

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    3. and references therein

    1. N-Acetyl-indoxyl acceptor is more likely present in the keto form in non-polar and aprotic solvents, which was confirmed in 1H NMR spectrum measured in this study (see ESI†)