Monosaccharides Derivatives PDF

# Monosaccharides Derivatives ## Monosaccharides Derivatives 1. Sugar acids 2. Deoxy sugars 3. Sugar alcohols 4. Amino sugars 5. Ester formation 6. Glycosidic linkage ## Sugar acids - **Sugar acid** The monosaccharides may be oxidized to yield different sugar acids depending upon the oxidation...

# Monosaccharides Derivatives ## Monosaccharides Derivatives 1. Sugar acids 2. Deoxy sugars 3. Sugar alcohols 4. Amino sugars 5. Ester formation 6. Glycosidic linkage ## Sugar acids - **Sugar acid** The monosaccharides may be oxidized to yield different sugar acids depending upon the oxidation conditions. Mild chemical oxidation converts the aldehyde group into a carboxylic acid group at C-1 of aldoses, thereby yielding aldonic acids, e.g. gluconic acid. Oxidation at C-6 yields an alduronic (uronic) acid, e.g. glucuronic acid, while oxidation at both C-1 and C-6 generates the saccharic or aldaric acids, e.g. glucaric acid. Sugar acid derived from aldoses sugars **0** **H** **COOH** - **Oxidation of carbon 1** - **It occurs when** **oxidation to carbon 1 = Aldonic sugars** HO **H** HO **-H** **H** **OH** **H** **OH** **Br₂H₂O** **[0]** HO **H** HO **H** HO **H** HO **H** **CH₂OH** **CH₂OH** **L-Glucose** **Gluconic Acid** - **Oxidation of C6 (primary alcohol) gives uronic acid** **Protection** **De protection** **CHO** **CHO** **CHO** **H- OH** **H- -OH** **HOH** **HO -H** **Br** **HO** **-H** **HO** **H** **H-** **-OH** **H-** **OH** **H** **OH** **HOH** **H** **-OH** **H** **-OH** **H** **OH** **HOO** **D-Glucose** **HO** **D-Glucuronic acid** **OH** - **Oxidation of C1 and C6 gives saccharic glucaric acid** **COOH** **H-C-OH** **12** **13** **H-C-OH** **HO-C-H** **13** **HO-C-H** **H-C-OH** **Oxidation** **15** **H-C-OH** **16** **CH2OH** **D-Glucose** **COOH** **Aldaric of Glucose** **H-C-OH** **H-C-OH** **16** - **Vitamin C (L-Ascorbic acid)** - It is a one of uronic sugar and one oof the most important sugar derivatives - Ascorbic acid is an organic compound with formula C6H8O6, originally called hexuronic acid. HO HO 0 HO OH ## Deoxy sugar - **Deoxy sugar, meaning that it is derived from the sugar by loss of a hydroxy group.** - **The most important deoxy sugar is deoxyribose** - **Ribose is the main sugar in thee structure of RNA while Deoxyribose is the main sugar of DNA, 2-deoxyribose derivatives have an important role in biology** ## Deoxy sugar **=0** **HO** **I** **OH** **H** **OH** **H** **OH** **I** **H-0-0-0-0-C-H** **II** **5CH2OH** **OH** **CH** **HO HO** **Ribose** **5CH2OH** **0** **OH** **H** **H** **H** **H** **OH** **OH H** **OH** **Deoxyribose** **OH** ## Sugar alcohol - **A sugar alcohol is a sugar with an alcohol group attached to it. They include erythritol, lactitol, maltitol, mannitol, sorbitol and xylitol identified by their "ol" suffix.** - **Sugar alcohols (also called polyhydric alcohols, polyalcohols) are organic compounds, typically derived from sugars, containing one hydroxyl group (-OH) attached to each carbon atom.** - **It is produced by reduction of monosaccharides (by adding H2) to the functional group replacing it with OH** ## Sugar Alcohol **D-Sorbitol** **CH₂OH** **D-Galactitol** **CH₂OH** **H** **OH** **Π** **OH** **T** **T** **H** **OH** **H** **T** **E** **H** **Оп OH** **H** **E** **T** **11** **OH** **H** **OH** **CH₂ON** **CH₂OH** ## Sugar Alcohol **0** **C-H** **CH2OH** **HO H** **HO H** **HO H** **NaBH4/H3O+** **HO H** **HOH** **Reduction** **H OH** **H- -OH** **H OH** **CH2OH** **CH2OH** **Mannose** **Mannitol** - **Glyceraldehyde????** - **Fructose ?????** ## Amino sugar - **If the OH group replaced by amino group in C2, the resulting sugar is called amino sugar** **CH2OH** **CH2OH** **HO** **0** **H** **0** **H** **H** **H** **OH H** **OH H** **H** **OH** **HO** **OH** **H NH** **Amino** **group** **H NH2** **Glucosamine** **Galactosamine** ## Amino sugars - **Three vital amino sugars are of physiological importance, namely glucosamine, galactosamine and neuraminic acid.** - **Amino sugar is one of components of glycolipids and glycoproteins** - **Glycosaminoglycans is a type of antibiotics e.g: Erythromicine, Azithromycin** ## Glycosidic linkage - **Glycosidic bond is a type of ether bond that joins a sugar to another group, which may or may not be another carbohydrate.** - **Gycosidic bonds formed by reaction of 2 OH group by removal of water** **OH group of anomeric** **carbon atom with other** **OH group** **anomeric** **OH carbon** **glycosidic** **If the OH from another** **sugar then it is called** **Glycon** **H** **-OH** **H** **-OH** **H** **OHH** **+ HO** **CH₃** **H** **→** **오** **H** **OH** **bond** **+중** **If the OH attached to OH** **of another compound then** **its called Aglycon** **HO** **오** **H운** **HO** **CH** ## Glycosidic Linkage **6** **CH₂OH** **7** **H5** **OH** **HOH.C** **0** **H** **4** **1** **2** **5** **HO** **OH** **13** **H** **0** **2** **H** **HO** **CH₂OH** **3** **4** **6** **H** **OH** **Glycosidic** **linkage** **OH** **H** **a-D-Glucose** **B-D - Fructose** **Alcohol** **Anomeric** **CH2OH** **carbon** **CH2OH** **5** **0** **5** **0** **H** **OH** **+** **OH** **HO** **OH** **HO** **OH** **3** **3** **OH** **OH** **a-D-(+)-glucose** **a-D-(+)-glucose** **(monosaccharides)** **CH2OH Glycosidic 6CH2OH** **linkage** **0** **0** **OH** **OH** **+ H₂O** **HO** **OH** **OH** **OH** **a-Maltose** **(disaccharide)** **Orientation of this -OH** **group identifies this** **disaccharide as a-maltose.** **CH2OH** **-OH** **-0** **HO** **1** **HO HO** ## Naming glycosidic bond - **Glycosidic bonds named according to 2 criteria:** 1. **Configuration of anomeric carbon atom( alfa or beta)** 2. **Number of carbon atom involved in the glycosidic linkage** **Glycosidic Linkage** **6** **CH₂OH** **1** **H5** **-OH** **HOH.C** **0** **H** **4** **1** **2** **OHH** **-0-** **HO 13 21** **H** **5** **HO/CH₂OH** **3** **4** **6** **H OH** **Glycosidic** **linkage** **H H** **a-D-Glucose** **B-D-Fructose** **Example:** **In this disaccharide the bond** **named as:** **(Alfa, 1,4 glycosidic bon)** ## Ester formation - **If the OH group of monosaccharides react with COOH of acid** - **Like reaction of phosphate group with OH of glucose it will give : Glucose 1- phosphate or Glucose 6-phosphate** **Glucose** **CHOH** **Hexokinase** **OH** **HỌ** **Glucose-6-phosphate** **O-P-O-** **OH** **OH** **Mg** **OH** **ATP** **ADP** **OH** **C6H12O6** **CH3OP** **shutterstock. com 2146115535** **H** **H** **P** **0** **0** **H** **OHH** **HHO** **HO** **OH** **H** **OH** **HOH** **OHH** **Glucose-6-Phosphate** **Fructose 1,6-Bis Phosphate** ## Summaries the derivatives of monosaccharides - **Oxidation leads to** - **Reduction leads to..** - **Amination leads to........** - **Reaction of OH with acid leads to..............** - **Removal of oxygen at C2 leads to** - **Congugation of OH of anomeric carbon with another OH...**