By Marco Brito Arias
This ebook includes the easiest identified methods for getting ready the most varieties of glycosides in a brief and finished learn. it is usually man made pathways of demanding glycosides often called antiviral or antineoplasic medicinal drugs, or artificial substrates used for enzymatic detection together with these used as substrates for detection of gene markers in plant biotechnology. particular cognizance is made at the structural characterization, delivering the elemental instruments for the structural project via NMR, X-Ray and mass spectra suggestions. the various chapters hide recommendations for instruction of antiviral and antineoplasic medications integrated in a drug layout direction.
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Extra info for Synthesis and Characterization of Glycosides
OEt2. 46. Synthesis of thiomonosaccharides. 3 Thiopyranoside Monosaccharides Thiosugars Sugars are another class of interesting carbohydrate mimetics. The synthesis of these derivatives can be achieved by using aldolases RAMA for the aldol condensation reaction.. 4 Carbapyranoside-Saccharides More recently this type of sugar mimics have received increasing attention since some of them present α-glucosidase activity and therefore considered for therapies for non-insulin-dependent diabetes mellitus.
Iv) a) FeCl3, Ac2O, – 20oC b) H2, Pd/C, EtOH. c) Ac2O, Py. v) NaBH4, CH2Cl2/MeOH, OoC. 48. Synthesis of carbapyranoside-disaccharides. 8. 49. Chemoenzymatic synthesis of pseudotrisaccharides. OH HO O X HO O(CH2)7CH3 OH OH 37 NHAc i OH HO X O O O(CH2)7CH3 OH OH NHAc O OH H3 C X=O X = NH HO OH i) fucosyltransferase, GDP-Fuc. 54,55 It has been found that in the absence of selective conditions, a leaving group can be found as a mixture of anomers, as in the case of the acetates. 52). 53). O OH O X X C C H H OH O C H X X O C H X = Halogen, sulfonyl, imidate, sulfur, acetate, etc.
Removed under basic and for the later neutral conditions, being the best conditions for preserving the glycosidic bond. The standard conditions for either installing and removing the most common protecting group described are: Acetate (Ac-): The standard procedure involves the use of acetic anhydride in the presence of pyridine or triethylamine as acid scavenger, and 4-(dimethylamino) pyridine (DMAP) that improves the rate of reaction. The cleavage of acetates proceeds smoothly with NaOMe solution also known as Zemplen conditions.
Synthesis and Characterization of Glycosides by Marco Brito Arias