Table 1.

Summary of solid-phase methods for glycan isolation

Linkage	Isolation method	Reference	Application	Pros and cons
Hydrazide	Formation of hydrazone between glycan and hydrazide; release of glycans by hydrolysis	Yang et al. [28]	N-glycan isolation from serum	Pros: conjugation and hydrolysis of glycans can be controlled by pH; fast capture and release Cons: reversible hydrazone bonds reduce glycan recovery
		Miura et al. [103]	O-glycan enrichment from mucin
		Lee et al. [104]	Carbohydrate microarray
Hydroxylamine	Formation covalent bonding between oxime and reducing end of glycans; release of glycan by hydrolysis	Thygesen et al. [30]	Oxime functionalized AuNP for protein–carbohydrate interactions	Pros: ease of formation under mild aqueous conditions; high nucleophilicity via the α-effect; good stability under a wide range of pH; versatility in the choice of supports Cons: difficulty due to reduced hydrolysis compared to hydrazone bond
		Vila-Perello et al. [58]	Immobilization of oligosaccharide on specific protein-carbohydrate sensor surface
		Dendane et al. [105]	Immobilization of oxime bond on to the inner wall of fused-silica capillary and on the surface of glass slides
Cysteinamide	Anchoring of cysteine-terminated resins through formation of a thiazolidine linkage	Guillaumie et al. [57,62]	Immobilized amine-bond of cysteinamide on solid-phase and capture glycan via thiazolidine linkage	Pros: quantitative coupling; thiazolidine stability over a wide range of conditions Cons: coupling in multiple steps
Disulfide	Formation of disulfide bond on solid-phase support; release of glycan through cleavage of disulfide bond	Guillaumie et al. [57,106,107]	(GalA)n functionalized sepharose supports; glycan reducing end conjugation with aminooxyacetamide	Pros: quantitative coupling of glycans; stable bond; glycan capture completion Cons: residue left on glycan reducing ends
Reductive alkylation	Formation of a chemoselective reductive alkylation of the 2-amino group; release of glycans by hydrolysis	Jensen et al. [72]; Rolborg et al. [108]	Unprotected D-glucosamine and glucosamine derivatives are attached to a trialkoxybenzyl linker on a solid support	Cons: quantitative coupling of glycans; good glycan capture yield; easy to release of glycans by hydrolysis at acid condition Pros: only suitable for glucosamine and its derivatives