The D-Aldoses: (CH 2 O) x : X = 3 to 6. Kiliani-Fisher Synthesis (CH 2 O) 3. D-glyceraldehyde. 1) HCN 2) DibalH or (CH 2 O) 4 H HO.
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1 The D-Aldoses: (C 2 ) : X = 3 to 6 (C 2 ) 3 Kiliani-Fisher Synthesis D-glyceraldehyde 1) C 2) Dibal 2, Pd/BaS 4 3) 3 + (C 2 ) 4 D-erythrose D-threose 1) C 2) Dibal 2, Pd/BaS 4 3) 3 + (C 2 ) 5 D-Ribose D-Arabinose D-Xylose D-Lyose 1) C 2) Dibal 2, Pd/BaS 4 3) 3 + 1) C 2) Dibal 2, Pd/BaS 4 3) 3 + (C 2 ) 6 D-Allose C-3-epi-glucose D-Glucose D-Gulose C-3,4-bis-epi-glucose D-Galactose C-4-epi-glucose D-Altrose C-2,3-bis-epi-glucose D-Mannose C-2-epi-glucose D-Idose C-2,3,4-tris-epi-glucose D-Talose C-2,4-bis-epi-glucose
2 eoses: (C 2 ) 6 α-heoses D-Glucose (C 2 ) 6 C C 2 C C 2 β-isomers fm fm is me stable! furanose fm α Mannose α-allose α-isomers fm is me stable! α-galactose α-gulose X =1; lone pair aligns with polarized bond cis so beta (β) Aial Me Stable! X =1; acid base catalyzed trans so alpha (α) Alpha (α)/beta (β) does not refer to either aial equatial. Alpha (α)/beta (β) refers to the cis/trans relationship between the anomeric hydroyl group and the terminal carbon when the sugar is in a cyclized fm between the hydroyl group on the penultimate carbon and the carbonyl. Usually the α-isomer is me stable than the β- isomer α-idose α-altrose α-talose 2-pyran 4-pyran tetrahydropyran furan tetrahydro-furan Maltose (glu/glu)
3 eoses: (C 2 ) 6 Usually the α-isomer is me stable than the β- isomer X =1; lone pair aligns with polarized bond Mecahnism f anomer isomerization cis so beta (β) Aial Me Stable! acid base catalyzed X =1; trans so alpha (α) Alpha (α)/beta (β) does not refer to either aial equatial. Alpha (α)/beta (β) refers to the cis/trans relationship between the anomeric hydroyl group and the terminal carbon when the sugar is in a cyclized fm between the hydroyl group on the penultimate carbon and the carbonyl equatial atack aial atack 2 Mecahnism f α-glycoside synthesis + R R R aial atack R
4 Carbohydrates: (C 2 ) The eoses (C 2 ) 6 D-Glucose (C 2 ) 6 C C 2 C C 2 L-Glucose (C 2 ) 6 C C 2 C C 2 2-pyran 4-pyran tetrahydropyran furan tetrahydro-furan fm furanose fm β-isomer Usually the α-isomer is me stable than the β- isomer fm is me stable! β-isomer α-isomer fm is me stable! α-isomer L-Sugars β-heoses L-Sugars α-heoses Glucose all equatial pyran substituents β-glucose β-glucose
5 The eoses L-Sugars β-heoses L-Sugars α-heoses Glucose all equatial pyran substituents β-glucose β-glucose Mannose C-2 epi-glucose C-2 aial β Mannose β Mannose α Mannose α Mannose Allose C-3 epi-glucose C-3 aial β-allose β-allose α-allose α-allose Galactose C-4 epi-glucose C-4 aial β-galactose β-galactose α-galactose α-galactose Gulose C-3/4 epi-glucose C-3/4 aial 's β-gulose β-gulose α-gulose α-gulose Idose C-2/3/4 epi-glucose C-2/3/4 aial 's β-idose β-idose α-idose α-idose Altrose C-2/3 epi-glucose C-2/3 aial 's β-altrose β-altrose α-altrose α-altrose Talose C-2/4 epi-glucose C-2/4 aial 's β-talose β-talose α-talose α-talose
6 Carbohydrates: (C 2 ) 5 The Pentoses: (C 2 ) 5 Carbohydrate ptions of DA nd RA α/β-d-ribose 2-Deoy-α/β-D-Ribose D-Arabinose (C 2 ) 5 D-Arabinose C C 2 C C 2 α/β-d-arabinose cis so Beta (β) Pyranose fm D-Ribose (C 2 ) 5 D-Ribose C C 2 C C 2 trans so alpha (α) α/β-d-ribose Pyranose fm Alpha (α)/beta (β) does not refer to either aial equatial. D-Xylose (C 2 ) 5 D-Xylose C C 2 C C 2 Alpha (α)/beta (β) refers to the cis/trans relationship between the anomeric hydroyl group and the terminal carbon when the sugar is in a cyclized fm between the hydroyl group on the penultimate carbon and the carbonyl. α/β-d-xylose Pyranose fm D-Lyose (C 2 ) 5 D-Lyose C C 2 C C 2 α/β-d-lyose Pyranose fm
7 The Disaccharides Maltose (glu/glu) Cellobiose (glu/glu) Lactose (gal/glu) β-1,3'-glycosyl linkage C 2 2 Ac 2-acetyl-glucosamine (gluac) yalobiuronic Acid 2 C glucuonic acid Blood-type Di/Trisaccharides Ac Membrane Protein Membrane Protein Membrane Protein Blood type-a Blood type-b Blood type- Ac -Acetylgalactosamine (galac) 6-deoy-galactose
8 The ligosaccharides Amylose (glu) Cellulose (glu) Ac Ac Ac Chitin (gluac) Ac 2-acetylamino-2-deoy-glucose (gluac) The clinicaly used ligosaccharides C 2 Ac C 2 yaluronic Acid anticoagulant Ac C 2 2 C 2 yalobiuronic Acid 3 S S 3 C 2 S 3 3 S 3 S heparin 3 S C 2 Ac 2 C 2-acetyl-glucosamine (gluac) glucuonic acid Aminoglycoside Antibiotics: Deoy/Amino Sugars R R' Kanamycin A: R = 2, R'= B: R = 2, R'= 2 C: R =, R'= Tobramycin Dibekacin 2 Amino Sugars
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