Evolution of glycosaminoglycans

Figures & data

Figure 1 The backbone structure of GAGs. CS or DS is composed of alternating disaccharide units of GlcA or IdoA and GalNAc, respectively. R₁, R₂, R₃, R₄ = −H or −SO₃H. Modification with β-D-glucose at the R₂ position has been found in squid CS. The presence of the α-L-fucose branch at the R₄ position has been reported in the CS preparations from sea cucumber and king crab. HS is composed of alternating disaccharide units of GlcA or IdoA and GlcN. R₁ = −COCH₃ or −SO₃H; R₂, R₃, R₄, R₅ = −H or −SO₃H. Recently, sulfation at the R₅ position was discovered in a bivalve HS.71 HA is a linear polymer composed of GlcA and GlcNAc.

Figure 2 Distribution of GAGs in the animal kingdom.

Table 1 Representative disaccharide composition of CD/DS from various species

Class	Species	Disaccharide unitsa							Sulfate/disaccharideb	Reference
		O	A	C	B	D	E	Others
Coelenterata	Hydra magnipapillata	71c	15c	14c					0.29	25
Coelenterata	Hydra magnipapillata (nematocyst)	100c							0	26
Nematoda	Caenorhabditis elegans	100c							0	28
Echinodermata	Strongylocentrotus purpuratus (embryo)		7d	19d			74d		1.74	36
Echinodermata	Strongylocentrotus purpuratus (adult)			59d	16d		25d		1.41	36
Annelida	Eisenia Andrei	3	76	6	15				1.12	46
Tunicata	Ascidia nigra			10d<		>90d			1.90	47
Tunicata	Styela plicata		28d	1d	66d	5d			1.71	48
Mollusca	Thysanoteuthis rhombus (arms)	88	6	2			4		0.16	63
Mollusca	Thysanoteuthis rhombus (skin)	17	26	19			38		1.21	63
Mollusca	Thysanoteuthis rhombus (head)	33	31	15			21		0.88	63
Mollusca	Thysanoteuthis rhombus (eyes)	13	52	13			22		1.09	63
Mollusca	Anodonta anodonta	26	46	28					0.74	67
Mollusca	Scapharca inaequivalvis	17	51	4	21	2	1	U units 2%, T units 2%	1.11	72
Mollusca	Sepia officinalis (cornea)	11	52	9		28			1.17	86
Mollusca	Cipangopaludina chinensis	59	38	3					0.41	87
Mollusca	Viviparus ater	42	48	5			5		0.63	88
Chelicerata	Trachypleus tridentatus (gill)		46					K units 54%	1.54	79
Hexapoda	Drosophila melanogaster (adult)	71	29						0.29	17
Hexapoda	Anopheles stephensi (female)	73	27						0.27	83

a Disaccharide units present in CS/DS chains are shown by the symbols: O, HexA-GalNAc; A, HexA-GalNAc(4-O-sulfate); C, HexA-GalNAc(6-O-sulfate); B, HexA(2-O-sulfate)-GalNAc(4-O-sulfate); D, HexA(2-O-sulfate)-GalNAc(6-O-sulfate); E, HexA-GalNAc(4, 6-O-disulfate); U, HexA(2-O-sulfate)-GalNAc; T, HexA(2-O-sulfate)-GalNAc(4, 6-O-disulfate); K, GlcA(3-O-sulfate)-GalNAc(4-O-sulfate).

b Total sulfate groups/disaccharides are given.

c The type of hexuronic acid in the disaccharide unit has been identified as GlcA.

d The type of hexuronic acid in the disaccharide unit has been identified as IdoA.

Table 2 Representative disaccharide composition of HS from various species

Class	Species	Disaccharide unitsa							Sulfate/disaccharideb	Reference
		0S	NS	6S	N,6S	N,2S	N,2,6S	Others
Coelenterata	Hydra magnipapillata	24	12	18	25	10	11		1.33	25
Nematoda	Caenorhabditis elegans	47	14	6		18	15		1.01	28
Annelida	Eisenia andrei		67		29		4		1.37	46
Tunicata	Styela plicata		11	14		22	53		2.28	52
Mollusca	Anomantidae sp.	33	29	19	19				0.86	65
Mollusca	Achatina fulica	10						2S units 90%	0.90	66
Mollusca	Callista chione			2	23	15	46	N,3,6S units 2%, Oligosc 12%		67
Mollusca	Anodonta anodonta			1	5	9	77	N,3,6S units 3%, Oligosc 5%		68
Mollusca	Tapes phylippinarum			2	4	6	81	N,3,6S units 2%, Oligosc 5%		89
Hexapoda	Drosophila melanogaster (adult)	31	27	3	18	17	4		0.29	17
Hexapoda	Anopheles stephensi (female)	39	24	5	20	9	3		0.96	83

a Disaccharide units present in HS chains are shown by the symbols: 0S, HexA-GlcNAc; NS, HexA-GlcN (2-N-sulfate); 6S, HexA-GlcNAc(6-O-sulfate); N,6S, HexA-GlcN(N-, 6-O-disulfate); N,2S, HexA(2-O-sulfate)-GlcN(2-N-sulfate); N,2,6S, HexA(2-O-sulfate)-GlcN(2-N-, 6-O-disulfate); 2S, HexA(2-O-sulfate)-GlcNAc; N,3,6S, HexA-GlcN(2-N-, 3-O-, 6-O-trisulfate).

b Total sulfate groups/disaccharide are given.

c The proportion of heparinase-resistant oligosaccharides is shown.

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