ketoses - Chem 234 Or ganic Chemist r y I I Pr ofessor...

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Chem 234 Organic Chemistry II Professor Duncan J. Wardrop University of Illinois at Chicago Spring 2003 H N N Cl O N 3 HO N NH O O CH 3 N H H N Br O O Br N O O N H H H H H O MeO O O OMe OMe O OMe O HO O O O O HO N CO 2 H S O HN NH H H H HO N N CF 3 CH 3 H 2 NSO 2 Cl Cl Cl OH
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25.9 Ketoses
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Ketoses Ketoses are carbohydrates that have a ketone carbonyl group in their open-chain form. C-2 is usually the carbonyl carbon. Ketotetroses CH 2 OH CHOH Ketotrioses CH 2 OH Ketopentoses Ketohexoses CH 2 OH CHOH CHOH CH 2 OH CH 2 OH CHOH CHOH CHOH CH 2 OH CH 2 OH CH 2 OH 1 2 3 1 2 3 1 2 3 1 2 3 4 5 4 4 5 6 O O O O
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Structure of D -Ribulose D -Ribulose CH 2 OH O H OH OH H CH 2 OH OH CH 2 OH O OH OH H H 1 α- -Ρ ιβυλοφυρανοσε ΧΗ 2 ΟΗ Ο Η Η 1 2 β- ΧΗ 2 Ο Η Η Η Η 1 2 3 4
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25.10 Deoxy Sugars
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Deoxy Sugars Often one or more of the carbons of a carbohydrate will lack an oxygen substituent. Such compounds are called deoxy sugars. CHO H OH 6-Deoxy- L -mannose OH H HO H HO H CH 3 CHO H H 2-Deoxy- D -Ribose OH H H CH 2 OH OH
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25.11 Amino Sugars
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Amino Sugars An amino sugar has one or more of its oxygens replaced by nitrogen. These molecules and the polysaccharides derived from them are often biologically active: groups interact strongly with acidic residues on proteins and receptors. OH O Me HO NH 2 L- Daunosamine O HO NH OH H OH HO CH 3 O N -Acetyl- D -glucosamine CHO H NHAc HO H H OH H OH CH 2 OH
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Streptomycin: Aminoglycoside Antibiotic Streptidine N -Methyl- D -glucosamine OH OH HN NH 2 NH H N H 2 N NH 2 HO O HO Me OHC O HO HO HO H N Me O H H L -Streptose
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Aminoglycoside Antibiotics O O O Me Me HO Me H OH Me OH Me O O Me Me O MeO Me OH Me Erythromycin - Antibiotic L-Daunosamine residue L-Mycarose residue COCH 3 OH O H OH OH O O MeO O H 3 C NH 2 HO Daunomycin - Antileukemic Agent O HO Me H 2 N L-Daunosamine residue
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25.12 Branched-Chain Carbohydrates
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Branched-Chain Carbohydrates Carbohydrates that don't have a continuous chain of carbon-carbon bonds are called branched-chain carbohydrates. OH O Me Me HO NH 2 L-Vancosamine CHO H OH CH 2 OH CH 2 OH HO O HO OH OH HO D-Apiose
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Vancomycin: Aminoglycoside Antibiotic OH N H H N N H H N N H O O O NH 2 O OH O H N Me Me Me HO OH O O O H HO O HN O HO O H H H H H Cl Cl O HO HO OH O O Me Me HO NH 2 Vancomycin - Antibiotic L-Vancosamine residue D- Glucose residue
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25.13 Glycosides
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O- Glycosides Glycosides have a substituent other than OH at the anomeric carbon. Usually atom connected to the anomeric carbon is oxygen. O HO HO O H OH HO H CHO H OH H HO D -Glucose H OH OH H CH 2 OH D -Glucopyranose O HO HO O H OH HO Me Methyl β -∆- Γ λυχοπψρανοσιδε Αλδεηψδε Ηεμ ιαχεταλ Αχεταλ Τηισ μ ολεχυλε ισ α γλψχοσιδε
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O- Glycosides O HO HO O H OH HO C Linamarin a cyanogenic O -glucoside found in the cassava plant CH 3 C CH 3 N Linamarase enzyme O HO HO O H OH HO H D -Glucopyranose C H 3 C CH 3 HO C N H 3 C O CH 3 H C N Hydrogen cyanide Cooking the grated cassava root reduces the level of linamarin through hydrolysis and makes this starch-rich food edible.
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ketoses - Chem 234 Or ganic Chemist r y I I Pr ofessor...

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