Carbohydrates
Monosaccharides
stereoisomers of monosaccharides
- unbranched carbon chains
- classification: { s t r u c t u r e : { a l d o s e 醛 醣 k e t o s e 酮 糖 n u m b e r : t r i o s e s , t e t r o s e s , p e n t o s e s , h e x o s e s , h e p t o s e s \begin{cases}structure:\begin{cases}aldose醛醣\\ketose酮糖\end{cases}\\ number:trioses, tetroses, pentoses, hexoses, heptoses\end{cases} ⎩⎪⎨⎪⎧structure:{aldose醛醣ketose酮糖number:trioses,tetroses,pentoses,hexoses,heptoses
- stereoisomers立体异构体:n chiral carbons → 2 n \rightarrow 2^n →2n stereoisomers
- { { e n a n t i o m e r s 对 映 异 构 体 : 镜 像 对 称 d i a s t e r e o m e r s 非 对 映 体 e p i m e r s 差 向 异 构 体 : 仅 在 一 个 碳 异 构 的 两 种 糖 \begin{cases}\begin{cases}enantiomers对映异构体: 镜像对称\\diastereomers非对映体\end{cases}\\epimers差向异构体:仅在一个碳异构的两种糖\end{cases} ⎩⎪⎨⎪⎧{enantiomers对映异构体:镜像对称diastereomers非对映体epimers差向异构体:仅在一个碳异构的两种糖
- the way to represent them
- ball-and-stick models
- fischer projection formulas横前竖后
- perpective formulas
- DL
- the reference carbon: the chiral center most distant from the carbonyl carbon
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-OH isomer right D left L
- RS
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4 ⟶ \longrightarrow ⟶ 3 ⟶ \longrightarrow ⟶ 2 ⟶ \longrightarrow ⟶ 1 − H , − D , − T , − C H 3 , − C 6 H 5 , − C H 2 O H , − C H R O H , − C H O , − C O N H 2 , − C O O H , − C O O R , − N H 2 , − N H R , − O H , − O R , − O C O R , − S H -H, -D, -T, -CH_3, -C_6H_5, -CH_2OH, -CHROH, -CHO, -CONH_2, -COOH, -COOR, -NH_2, -NHR, -OH, -OR, -OCOR, -SH −H,−D,−T,−CH3,−C6H5,−CH2OH,−CHROH,−CHO,−CONH2,−COOH,−COOR,−NH2,−NHR,−OH,−OR,−OCOR,−SH - R：顺时针；L：逆时针
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cyclization of monosaccharides
- aldehyde + alcohol
⟷
\longleftrightarrow
⟷ hemiacetal
⟷
\longleftrightarrow
⟷ acetal
ketone + alcohol ⟷ \longleftrightarrow ⟷ hemiketal ⟷ \longleftrightarrow ⟷ ketal
- the position of the hydroxylgroup on the anomeric carbon: { o p p o s i t e : α s a m e : β \begin{cases}opposite:\alpha \\same:\beta \end{cases} {opposite:αsame:β
- pyranoses and furanoses
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n-membered oxygen-containing rings name six pyranoses five furanoses
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- how are the carbon chains shown as Haworth perspective formulas
- left → \rightarrow → up
- right → \rightarrow → down
- − C H 2 O H → -CH_2OH \rightarrow −CH2OH→ up (D)
- − C H 2 O H → -CH_2OH \rightarrow −CH2OH→ down (L)
- the anomeric carbon of sugar acting as reducing agents
- Fehling’s test(alkaline conditions)
process F e 3 + → F e 2 + Fe^{3+}\rightarrow Fe^{2+} Fe3+→Fe2+ C u 2 + → C u + Cu^{2+}\rightarrow Cu^{+} Cu2+→Cu+ carbonyl carbon → \rightarrow → carboxyl group
- Fehling’s test(alkaline conditions)
- colorimetric glucose analysis
- 测量还原糖含量
representative monosaccharides
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{ D − G l y c e r a l d e h y d e 甘 油 醛 D − E r y t h r o s e 赤 鲜 糖 D − R i b o s e 核 糖 ， D − A r a b i n o s e 阿 拉 伯 糖 ， D − X y l o s e 木 糖 D − G l u c o s e 葡 萄 糖 ， D − M a n n o s e 甘 露 糖 ， D − G a l a c t o s e 半 乳 糖 \begin{cases}D-Glyceraldehyde甘油醛\\D-Erythrose赤鲜糖\\D-Ribose核糖，D-Arabinose阿拉伯糖，D-Xylose木糖\\ D-Glucose葡萄糖，D-Mannose甘露糖，D-Galactose半乳糖\end{cases} ⎩⎪⎪⎪⎨⎪⎪⎪⎧D−Glyceraldehyde甘油醛D−Erythrose赤鲜糖D−Ribose核糖，D−Arabinose阿拉伯糖，D−Xylose木糖D−Glucose葡萄糖，D−Mannose甘露糖，D−Galactose半乳糖
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{ D i h y d r o x y a c e t o n e 二 羟 基 丙 酮 D − E r y t h r u l o s e 赤 藓 酮 糖 D − R i b u l o s e 核 酮 糖 ， D − X y l u l o s e 木 酮 糖 D − F r u c t o s e 果 糖 \begin{cases}Dihydroxyacetone二羟基丙酮\\D-Erythrulose赤藓酮糖\\D-Ribulose核酮糖，D-Xylulose木酮糖\\D-Fructose果糖\end{cases} ⎩⎪⎪⎪⎨⎪⎪⎪⎧Dihydroxyacetone二羟基丙酮D−Erythrulose赤藓酮糖D−Ribulose核酮糖，D−Xylulose木酮糖D−Fructose果糖
Hexose Derivatives
oligosaccharides
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type feature representation reducing disaccharides with free anomeric carbon maltose(Glc( α 1 → 4 \alpha 1\rightarrow 4 α1→4)Glc), lactose(Gal( β 1 → 4 \beta 1\rightarrow 4 β1→4)Glc) nonreducing disaccharides anomeric carbon invovled in the glycosidic linkage sucrose(Fru( 2 β ↔ α 1 2\beta \leftrightarrow \alpha 1 2β↔α1)Glc), trehalose(Glc( α 1 ↔ 1 α \alpha 1\leftrightarrow 1\alpha α1↔1α)Glc)
polysaccharides
homopolysaccharides同（聚）多糖
- srorage homopolysaccharides
- glycogen糖原
- starch淀粉(amylose直链淀粉、amylopectin支链淀粉)
- structural homopolysaccharides
- dextran葡聚糖
- cellulose纤维素
- chitin几丁质
-
name component chains node character glycogen glucose α 1 → 4 \alpha 1\rightarrow 4 α1→4, about 8-12 residues α 1 → 6 \alpha 1 \rightarrow 6 α1→6 only one reducing end starch(amylose) glucose α 1 → 4 \alpha 1\rightarrow 4 α1→4 / one reducing end starch(amylopectin) glucose α 1 → 4 \alpha 1\rightarrow 4 α1→4, about 24-30 residues α 1 → 6 \alpha 1 \rightarrow 6 α1→6 only one reducing end dextran glucose α 1 → 6 \alpha 1\rightarrow 6 α1→6 α 1 → 3 \alpha 1\rightarrow 3 α1→3(some have α 1 → 2 \alpha 1\rightarrow 2 α1→2 or α 1 → 4 \alpha 1\rightarrow 4 α1→4) formed by bacteria cellulose glucose β 1 → 4 \beta 1\rightarrow 4 β1→4 / can be broken by enzyme cellulase chitin N-acetylglucosamine β 1 → 4 \beta 1\rightarrow 4 β1→4 / water-insoluble
heteroploysaccharides杂多糖
- peptidoglycan肽聚糖
- agar琼脂
- agarose琼脂糖
- agaropectin琼脂胶
- glycoasminoglycans氨基葡聚糖
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name component chains node character peptidoglycan N-acetylglucosamine(GlcNAc乙酰葡萄糖胺), N-acetylmuranmic acid(Mur2Ac乙酰胞壁酸) β 1 → 4 \beta1\rightarrow 4 β1→4 cross-linked by short peptides can be hydrolyzing by the enzyme lysozyme agarose D-galactose, L-galactose derivative α 1 → 3 \alpha 1\rightarrow 3 α1→3(C-3 and C-6) / in some seaweeds agaropectin D-galactose, L-galactose derivative α 1 → 3 \alpha 1\rightarrow 3 α1→3(C-3 and C-6) branched in some seaweeds - glycosaminoglycans(GAGs)氨基葡聚糖
name compoenet small chain node character hyaluronate透明质酸 D-glucuronic acid葡萄糖醛酸, N-acetyl-glucosamine乙酰葡萄糖胺 β 1 → 3 \beta 1\rightarrow 3 β1→3 β 1 → 4 \beta 1\rightarrow 4 β1→4 serve as lubricants chondroitin sulfate硫酸软骨素 β 1 → 3 \beta 1\rightarrow 3 β1→3 β 1 → 4 \beta 1\rightarrow 4 β1→4 contribute to the tensile dermatan sulfate α 1 → 3 \alpha 1\rightarrow 3 α1→3 β 1 → 4 \beta 1\rightarrow 4 β1→4 contribute to the pliabity keratan sulfate硫酸角质素 β 1 → 4 \beta 1\rightarrow 4 β1→4 β 1 → 3 \beta 1\rightarrow 3 β1→3 have no uronic acid heparin肝素 α 1 → 4 \alpha 1\rightarrow 4 α1→4 α 1 → 4 \alpha 1\rightarrow 4 α1→4 anticoagulant heparan sulfate硫酸乙酰肝素 β 1 → 4 \beta 1\rightarrow 4 β1→4 α 1 → 4 \alpha 1\rightarrow 4 α1→4 sequence heterogeneity不均一性
glycoconjugates糖复合物
glycoproteins（糖蛋白GPs）
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a protein with small oligosaccharides attached
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anomeric carbon attached to amino acid
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name symbol O-linked oligosaccharides one yellow square N-linked oligosaccharides two blue square 
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lectin凝集素
glycolipid糖脂:lipopolysaccharides脂多糖
proteoglycans(PG蛋白聚糖)
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different GAGs are covalently linked to the core protein
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trisaccharide bridge:Gal → \rightarrow →Gal → \rightarrow →Xyl
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aggrecan聚集蛋白聚糖
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