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. 2018 Mar 25:10.1002/cbic.201800037.
doi: 10.1002/cbic.201800037. Online ahead of print.

Microarray Analysis of Oligosaccharide-Mediated Multivalent Carbohydrate-Protein Interactions and Their Heterogeneity

Madhuri Gade  1 , Catherine Alex  1 , Shani Leviatan Ben-Arye  2 , João T Monteiro  3 , Sharon Yehuda  2 , Bernd Lepenies  3 , Vered Padler-Karavani  2 , Raghavendra Kikkeri  1
Affiliations

Microarray Analysis of Oligosaccharide-Mediated Multivalent Carbohydrate-Protein Interactions and Their Heterogeneity

Madhuri Gade et al. Chembiochem. .

Abstract

Carbohydrate-protein interactions (CPIs) are involved in a wide range of biological phenomena. Hence, the characterization and presentation of carbohydrate epitopes that closely mimic the natural environment is one of the long-term goals of glycosciences. Inspired by the multivalency, heterogeneity and nature of carbohydrate ligand-mediated interactions, we constructed a combinatorial library of mannose and galactose homo- and hetero-glycodendrons to study CPIs. Microarray analysis of these glycodendrons with a wide range of biologically important plant and animal lectins revealed that oligosaccharide structures and heterogeneity interact with each other to alter binding preferences.

Keywords: C-type lectin; heterogeneity; mannose; microarray; oligosaccharides.

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Conflict of interest statement

Conflict of Interest

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Microarray analysis of M1 to M10 with plant and animal lectins. A) Bio-ConA, B) Bio-GNL, C) Bio-PNA, D) galectin-1, E) DC-SIGN-Fc, F) SIGNR3-Fc and G) MGL-1-Fc.
Figure 2
Figure 2
Principal component analysis of the fluorescence intensity of glycodendron binding with lectins. Inset: A screen plot of the percentage variance explained by each principal component.
Scheme 1
Scheme 1
Synthesis of glycodendrons M1 to M4. a) NIS, TfOH, 6-azidohexan-1-ol; b) PPh3, THF, water, Boc2O; c) TFA (20%) in CH2Cl2; d) 6-azidohexan-1-ol, BF3·Et2O; PPh3, THF, water, Boc2O; e) 10′, Et3N, CH2Cl2, RT; TEA in CH2Cl2; NaOMe, MeOH; f) 11′, Et3N, CH2Cl2, RT; TEA in CH2Cl2; NaOMe, MeOH; g) 12′, Et3N, CH2Cl2, RT; TEA in CH2Cl2; NaOMe, MeOH; h) 15′, Et3N, CH2Cl2, RT; TEA in CH2Cl2; NaOMe, MeOH.
Scheme 2
Scheme 2
Synthesis of glycodendrons M5 to M10. a) 10′, Et3N, CH2Cl2, RT; b) 11′, Et3N, CH2Cl2, RT; c) 12′, Et3N, CH2Cl2, RT; d) 15′, Et3N, CH2Cl2, RT; e) 15′, Et3N, CH2Cl2, RT; TEA in CH2Cl2; NaOMe, MeOH; f) 10′, Et3N, CH2Cl2, RT; TEA in CH2Cl2; NaOMe, MeOH; g) 11′, Et3N, CH2Cl2, RT; TEA in CH2Cl2; NaOMe, MeOH; h) 12′, Et3N, CH2Cl2, RT; TEA in CH2Cl2; NaOMe, MeOH.
See this image and copyright information in PMC

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