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Sea Sponges Cures Cancer? -The Synthesis of novel glycolipid analogues of α-Galactosyl Ceramide.

Sea Sponges Cures Cancer? -The Synthesis of novel glycolipid analogues of α-Galactosyl Ceramide.

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Isolated from a marine sponge Agelas mauritianus, α-Galactosyl Ceramide (α-GalCer) is a bioactive glycolipid that has therapeutic effects against bacteria, viruses, and autoimmune diseases.1 Therefore the synthesis of analogues is an area of obvious interest. Two glycolipid analogues of α-GalCer were successfully synthesised with potentially higher activities than that of α-GalCer.


1.Hung et al. Biochem. Pharm. 2007, 73, 1957-1970.
Isolated from a marine sponge Agelas mauritianus, α-Galactosyl Ceramide (α-GalCer) is a bioactive glycolipid that has therapeutic effects against bacteria, viruses, and autoimmune diseases.1 Therefore the synthesis of analogues is an area of obvious interest. Two glycolipid analogues of α-GalCer were successfully synthesised with potentially higher activities than that of α-GalCer.


1.Hung et al. Biochem. Pharm. 2007, 73, 1957-1970.

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Published by: Undergraduate Awards on Sep 01, 2012
Copyright:Attribution Non-commercial

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10/27/2013

 
Department of Chemistry National University of Ireland, Maynooth
Sea Sponges Cure Cancer?-Synthesis of Novel Glycolipid Analogues of α-Galactosyl Ceramide.
Roisin O Flaherty
4
th
Year B. Sc (Single Honours)February 2008.Supervisor:
Dr.
 
Trinidad Velasco Torrijos
Head of Department
: Prof. John Lowry‘Project submitted to the National University of Ireland Maynooth in fulfillment of theRequirements for the B.Sc. Single Honours degree in Chemistry.’
 
Contents Page:
DeclarationiAcknowledgementsiiAbbreviations and Keywords iii1. Abstract 12. Introduction and literature review2.1. Biology22.2. The importance of α-Galactosyl Ceramide32.3. Reaction Involving the Sugar Moiety2.3.1. S
 N
2 Reactions62.3.2. Koenigs-Knorr Reaction62.4. Activation and coupling for Peptide Bond Formation2.4.1. Carbodiimide Reagents72.4.2. Phosphonium and Uronium reagents82.4.3. Acid halogenating reagents92.4.4. Racemisation suppressants92.5. Overall aims of the project103. Experimental Section3.1. General Procedures3.1.1. Reagents113.1.2. Equipment113.2. 2,3,4,6-tetra-
O
-acetyl-1-bromo-α-D-galactopyranose 1 (ROF 3.1)123.3. 2,3,4,6-tetra-
O
-acetyl-1-O-docosanyl-β-D-galactopyranose 2 (ROF 8.1)133.4. N-tert-butoxycarbonyl-L-serine tetradecyl amide 3 (ROF 6.1)143.5. 2,3,4,6-tetra-
O
-acetyl-α,β-galactopyranose 4 (ROF 11.1)153.6. 2,3,4,6-tetra-
O
-(2,2,2-trichloro-acetmidoyl)-α-D-galactopyranose 5(ROF 12.1)163.7. 2,3,4,6-tetra-
O
-acetyl-1-
O
-[2-
tert 
-butoxycarbonylamino-2-tetra decyl-carbamoyl-(S)-ethyl-β-D-galactopyranose 6 (ROF 14.1)174. Results and Discussion4.1. Synthesis of glycolipid 219
 
4.1.1. Synthesis of glycosyl halide 1204.1.2. Synthesis of glycolipid 2224.2. Synthesis of amino acid glycolipid 6264.2.1. Synthesis of dipeptide unit 3274.2.2. Synthesis of imidate sugar donor 5304.2.3. Synthesis of glycolipid 6334.3. General Discussion375. Conclusion38References39Appendicesi

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