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寡糖

寡糖又称为低聚糖,是由2至10个相同或不同的单糖单位通过糖苷键连接起来形成的直链或含分支链的糖类化合物。尽管寡糖和单糖在物理及化学性质上相似,它们都易溶于水,并且很多低聚糖具有甜味,可被费林溶液氧化;不同之处在于它们在水解后能产生十个以下的单糖分子。

根据单糖单位的数量,寡糖可分为双糖、三糖、四糖和五糖等。构成寡糖的单糖可以相同也可以不同,与一般的糖苷不同的是,它们的配基也是糖。例如,蔗糖为典型的双糖,棉子糖为三糖,水苏糖为四糖,毛蕊花糖为五糖。

寡糖易溶于水或其他极性溶剂,并且分为还原性和非还原性两类,在生物体内从单糖逐步合成或由多糖降解产生。在植物细胞壁中的结构多糖,在病原体入侵时会分解成为具有生物活性的碎片,被称为寡糖素(oligosaccharin),对植物起保护和调节作用。

最常见的三糖是棉子糖,广泛存在于甜菜和棉籽中。制造蔗糖过程中产生的糖浆是提取棉子糖的良好原料。棉子糖水解后会得到半乳糖、葡萄糖及果糖各一分子。棉子糖是非还原性糖,其分子内的葡萄糖与果糖通过半缩醛羟基相连,而半乳糖则与葡萄糖之间形成1,6-糖苷键,结合顺序如下:半乳糖–(1->6)–葡萄糖–(1->2)–果糖。

水苏糖是自然界中重要的四糖之一,在棉子糖分子中通过6→1糖苷键在半乳糖的基础上连接一个半乳糖形成。类似地,还可以依次添加α-D-半乳糖生成五糖、六糖和七糖等同系物。这些水苏糖及其同系物都是植物的抗冻物质。

中文名称 英文名称 CAS号 化学式 结构式图片
—— methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 73960-72-2 C20H27NO12
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
—— α,α-trehalose (dihydrate form) 6138-23-4 C12H22O11*2H2O
α,α-trehalose (dihydrate form)
—— α,α-trehalose*2D2O 6138-23-4 C12H22O11*.2(2)H2O
α,α-trehalose*2D2O
—— stachyose hydrate 10094-58-3 C24H42O21*H2O
stachyose hydrate
—— alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1.fwdarw.6)-, pentahydrate 17629-30-0 C18H32O16.5H2O
alpha-D-Glucopyranoside, beta-D-fructofuranosyl O-alpha-D-galactopyranosyl-(1.fwdarw.6)-, pentahydrate
—— Kestose, 1- 470-69-9 C18H32O16
Kestose, 1-
—— (2R,3R,4S,5R)-2,3,5,6-tetrahydroxy-4-[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal 13117-26-5 C12H22O11
(2R,3R,4S,5R)-2,3,5,6-tetrahydroxy-4-[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
—— (2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal 3371-50-4 C18H32O16
(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal
—— D-Glucoheptose 62475-58-5 C7H14O7
D-Glucoheptose
—— GlcNAc1-beta-3GalNAc 95673-98-6 C16H28N2O11
GlcNAc1-beta-3GalNAc
—— N-[2-[5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide 125455-64-3 C22H31N3O13
N-[2-[5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
—— d-Mannoheptose 7634-39-1 C7H14O7
d-Mannoheptose
—— GlcNAc beta(1-3)GalNAc-alpha-pNP 125455-64-3 C22H31N3O13
GlcNAc beta(1-3)GalNAc-alpha-pNP
—— (2R,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol 39300-87-3 C14H26O11
(2R,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol
—— sodium;(2S,3S,4R,5S,6S)-2,3,4,5,6,7-hexahydroxyheptanoate 31138-65-5 C7H13NaO8
sodium;(2S,3S,4R,5S,6S)-2,3,4,5,6,7-hexahydroxyheptanoate
—— D-Raffinose Pentahydrate 17629-30-0 C18H32O16.5H2O
D-Raffinose Pentahydrate
—— Sodium (2R,3R,4R,5S,6R)-2,3,4,5,6,7-hexahydroxyheptanoate 31138-65-5 C7H13NaO8
Sodium (2R,3R,4R,5S,6R)-2,3,4,5,6,7-hexahydroxyheptanoate
—— 4-Nitrophenyl maltopentaoside 66068-38-0 C36H55NO28
4-Nitrophenyl maltopentaoside
—— [(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecaacetyloxy-10,15,20,25,30,35-hexakis(acetyloxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methyl acetate 23739-88-0 C84H112O56
[(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecaacetyloxy-10,15,20,25,30,35-hexakis(acetyloxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methyl acetate
—— N-(3,5-Dimethyltricyclo[3.3.1.1~3,7~]decan-1-yl)-4-O-alpha-L-erythro-hexopyranosyl-beta-D-threo-hexopyranosylamine 1159637-28-1 C24H41NO10
N-(3,5-Dimethyltricyclo[3.3.1.1~3,7~]decan-1-yl)-4-O-alpha-L-erythro-hexopyranosyl-beta-D-threo-hexopyranosylamine
—— Sucrose 6'-Acetate, Technical grade 80% 936001-72-8 C14H24O12
Sucrose 6'-Acetate, Technical grade 80%
—— 4-Nitrophenyl 2-Acetamido-3-O-(2-acetamido-2-deoxy-D-glucopyranosyl)-2-deoxy-a-D-galactopyranoside 125455-64-3 C22H31N3O13
4-Nitrophenyl 2-Acetamido-3-O-(2-acetamido-2-deoxy-D-glucopyranosyl)-2-deoxy-a-D-galactopyranoside
—— (2S,5R)-2-[[(3S,6R)-6-[(2S,4S,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol;pentahydrate 17629-30-0 C18H42O21
(2S,5R)-2-[[(3S,6R)-6-[(2S,4S,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol;pentahydrate
—— O-α-D-glucopyranosyl-(1-3)-O-<α-D-glucopyranosyl-(1-6)>-D-glucopyranose 3256-10-8 C18H32O16
O-α-D-glucopyranosyl-(1-3)-O-<α-D-glucopyranosyl-(1-6)>-D-glucopyranose
—— 3,6-Bis-<β-D-glucosido(1.5)>-D-glucose(1.5) 3256-10-8 C18H32O16
3,6-Bis-<β-D-glucosido(1.5)>-D-glucose(1.5)
—— O-β-Dglucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-α-D-glucopyranose 3256-10-8 C18H32O16
O-β-Dglucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-α-D-glucopyranose
—— tetra-N-acetyl-chitotetraose 2706-65-2 C32H54N4O21
tetra-N-acetyl-chitotetraose
—— penta-N-acetyl-chitopentaose 36467-68-2 C40H67N5O26
penta-N-acetyl-chitopentaose
—— stachyose 470-55-3 C24H42O21
stachyose
—— cellopentaose 2240-27-9 C30H52O26
cellopentaose
—— α-D-galactopyranosyl-(1->6)-O-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside pentahydrate 17629-30-0 C18H32O16*5H2O
α-D-galactopyranosyl-(1->6)-O-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside pentahydrate
—— 4-O-α-D-galactopyranosyl-α-D-galactopyranose 80446-85-1 C12H22O11
4-O-α-D-galactopyranosyl-α-D-galactopyranose
—— N-Acetyl-muraminsaeure 10597-89-4 C11H19NO8
N-Acetyl-muraminsaeure
—— Glc(a1-4)L-Glc(a1-4)L-Glc 1109-28-0 C18H32O16
Glc(a1-4)L-Glc(a1-4)L-Glc
—— L-Glc(a1-6)L-Glc(a1-6)L-Glc 3371-50-4 C18H32O16
L-Glc(a1-6)L-Glc(a1-6)L-Glc
—— Melezitose monohydrate 10030-67-8 C18H34O17
Melezitose monohydrate
—— Glc(a1-4)L-Glc(a1-4)L-Glc(a1-4)Glc 34612-38-9 C24H42O21
Glc(a1-4)L-Glc(a1-4)L-Glc(a1-4)Glc
—— 4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside 53643-14-4 C42H60N4O23
4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside
—— p-nitrophenyl β-cellotrioside 106927-48-4 C24H35NO18
p-nitrophenyl β-cellotrioside
—— p-nitrophenyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 84034-75-3 C32H39NO20
p-nitrophenyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
—— γ-cyclodextrin 17465-86-0 C48H80O40
γ-cyclodextrin
—— Neu5Acα(2-3)Galβ(1-4)GlcNAc 81693-22-3 C25H42N2O19
Neu5Acα(2-3)Galβ(1-4)GlcNAc
—— p-nitrophenyl-β-D-N,N',N''-triacetylchitotriose 7699-38-9 C30H44N4O18
p-nitrophenyl-β-D-N,N',N''-triacetylchitotriose
—— p-nitrophenyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside 59837-14-8 C20H28N2O13
p-nitrophenyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
—— hexa-O-acetyl-D-lactal 51450-24-9 C24H32O15
hexa-O-acetyl-D-lactal
—— 6-O-α-maltosylcyclomaltoheptaose 104723-60-6 C54H90O45
6-O-α-maltosylcyclomaltoheptaose
—— maltoheptaose 34620-78-5 C42H72O36
maltoheptaose
—— 4-O-<4-O-(6-O-α-D-Glucopyranosyl-α-D-glucopyranosyl)-α-D-glucopyranosyl>-D-glucose 34336-93-1 C24H42O21
4-O-<4-O-(6-O-α-D-Glucopyranosyl-α-D-glucopyranosyl)-α-D-glucopyranosyl>-D-glucose
—— D-(+)-xylobiose 6860-47-5 C10H18O9
D-(+)-xylobiose
—— Maltotetraose 38819-01-1 C24H42O21
Maltotetraose