Crystal Structures of β-1-N-Chloroacetamido Derivatives of D-Glucose and D-Galactose

Journal of Carbohydrate Chemistry

Volumn 22, Issue 9, 2003, Pages 891-901

  Aich, Udayanath ^a   Lakshmanan, Thiruneelakantan ^a   Varghese, Babu ^a   Loganathan, Duraikkannu ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

1 N Chloroacetamido sugar derivatives; Conformation; D galactopyranose; D glucopyranose; X ray crystal structure

Indexed keywords

AMIDE; CHLOROACETAMIDE; GALACTOSE; GLUCOPYRANOSIDE; GLUCOSE; GLYCOGEN PHOSPHORYLASE; HYDROGEN; PYRANOSIDE; SUGAR;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULE; TORSION; X RAY CRYSTALLOGRAPHY;

EID: 1642432896     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120026600     Document Type: Article

References (18)

1. Manger, I.D.; Rademacher, T.W.; Dwek, R.A. 1-N-Glycyl β-oligosaccharide derivatives as stable intermediates for the formation of glycoconjugate probes. Biochemistry 1992, 31, 10724-10732.
2. Manger, I.D.; Rademacher, T.W.; Dwek, R.A. Synthesis of 1-N-glycyl-β-oligosaccharide derivatives. Reactivity of Lens culinaris lectin with a fluorescent labeled streptavidin pseudoglycoprotein and immobilized neoglycolipid. Biochemistry 1992, 31, 10733-10740.
3. Likhosherstov, L.M.; Novokova, O.S.; Shibaev, V.N. Glycoconjugates of amines: alkylation of primary and secondary amines with N-chloroacetyl-β- glycopyranosylamines. Russ. Chem. Bull. 1998, 47, 1214-1217.
4. Likhosherstov, L.M.; Novokova, O.S.; Shibaev, V.N. Glycoconjugates of amino acids. Preparation through N-alkylation of amino acids with N-chloroacetyl-β-glycopyranosylamines. Russ. Chem. Bull. 1999, 48, 1365-1368.
5. Likhosherstov, L.M.; Novokova, O.S.; Shibaev, V.N.; Kochetkov, N.K. Synthesis of N-(chloroacetyl)-β-glycopyranosylamines derivatives of monosaccharides and lactose. Russ. Chem. Bull. 1996, 45, 1760-1763.
6. Watson, K.A.; Mitchell, E.P.; Johnson, L.N.; Cruciani, G.; Son, J.C.; Bichard, C.J.F.; Fleet, G.W.J.; Oikonomakos, N.G.; Kontou, M.; Zographos, S.E. Glucose analogue inhibitors of glycogen phosphorylase: from crystallographic analysis to drug prediction using GRID force-field and GOLPE variable selection. Acta Crystallogr. 1995, D51, 458-472.
7. Savel'ev, A.N.; Ibatyllin, F.M.; Eneyskaya, E.V.; Kachurin, A.M.; Neustroev, K.N. Enzymatic properties of α-D-galactosidase from Trichoderma reesei. Carbohydr. Res. 1996, 296, 261-273.
8. Sriram, D.; Lakshmanan, T.; Loganathan, D.; Srinivasan, S. Crystal structure of a hydrated N-glycoprotein linkage region model and its analogue: hydrogen bonding and π-π stacking driven molecular assembly. Carbohydr. Res. 1998, 309, 227-236.
9. Sriram, D.; Sreenivasan, H.; Srinivasan, S.; Vishnutheertha, M.; Priya, K.; Loganathan, D. β-1-N-Acetamido-D-glucopyranose. Acta Crystallogr., C 1997, 53, 1075-1077.
10. Delbaere, L.T.J. The molecular crystal structure of 4-N-(2-acetamido-2- deoxy-β-D-glucopyranosyl)-L-asparagine trihydrate and 4-N-(β-D- glucopyranosyl)-L-asparagine monohydrate. J. Biochem. 1974, 143, 197-205.
11. Priya, K. β-Galactosidase catalyzed oligosaccharides synthesis: transglycosylation to glycosylasparagine mimics and other acceptors. Ph.D. thesis; Indian Institute of Technology Madras: Chennai, 1999.
12. Koyama, Y.; Shimanouchi, T. The crystal and molecular structure of N-methylchloroacetamide. Acta Crystallogr. 1971, B27, 940-946.
13. Rao, V.S.R.; Qasba, P.K.; Balaji, P.V.; Chandrasekaran, R. Conformation of Carbohydrates; Harwood Academic: New York, USA, 2000.
14. Marchessault, R.H.; Perez, S. Conformations of the hydroxymethyl group in crystalline aldohexopyranoses. Biopolymers 1979, 18, 2369-2374.
15. Oikonomakos, N.G. Glycogen phosphorylase as a molecular target for type 2 diabetes therapies. Curr. Prot. Pept. Sci. 2002, 3, 561-586.
16. Isbell, H.S.; Frush, H.L. Mutarotation, hydrolysis and rearrangement reactions of glycosylamines. J. Org. Chem. 1958, 23, 1309-1315.
17. Sheldrick, G.M. SHELX97: Program for the Refinement of Crystal Structures; University of Gottingen: Gottingen, Germany, 1997.
18. Spek, A.L. PLATON: A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2000.