Abstract
X-ray crystallography is a powerful tool for obtaining molecular information regarding bond lengths, bond angles, hydrogen bond interactions, and torsion angles, which are necessary elements for understanding the conformation of glycosides. Improved diffractometers, faster computational processors, and mathematical programs have made possible the structural resolution of simple and complex substances of glycosidic nature particularly those with noncentrosymmetric space groups.
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Furberg S, Petersen CS (1962) Crystal and molecular structure of the p-bromophenylhydrazone of arabinose. Acta Chem Scand 16:1539–1548
Reeves RE (1950) The shape of pyranoside rings. J Am Chem Soc 72:1499–1506
Jeffrey GA, Pople JA, Binkley JS, Vishveshwara S (1978) Application of ab initio molecular orbital calculations to the structural moieties of carbohydrates. J Am Chem Soc 100:373–379
Jeffrey GA (1990) Crystallographic studies of carbohydrates. Acta Cryst B46:89–103
Cremer D, Pople JA (1975) General definition of ring puckering coordinates. J Am Chem Soc 97:1354–1358
Brown GM, Levy HA (1963) Sucrose: precise determination of crystal and molecular structure by neutron diffraction. Science 141:921–923
Leung F, Chanzy HD, Pérez S, Marchessault H (1976) Crystal structure of β-D-acetyl cellobiose, C28H38O19. Can J Chem 54:1365–1371
Brito-Arias MA, García-Baez EV, Durán-Páramo E, Rojas-Lima S (2002) Phenylmethyl 2,3,4-tri-O-acetyl-β-D-fucopyranoside. J Chem Crystallogr 32:237–241
Brito-Arias MA, Duran-Paramo E, Mata I, Molins E (2002) A comparative analysis of mono- and disaccharide benzyl fucopyranosides. Acta Cryst C58:o537–o539
Rencurosi A, Mitchell EP, Cioci G, Péres S, Pereda-Miranda R, Imberty A (2004) Crystal structure of tricolorin A: molecular rationale for the biological properties of resin glycosides found in some Mexican herbal remedies. Angew Chem Int Ed 43:5918–5922
Matijasic I, Pavlovic G, Trojko R Jr (2003) Methyl 3,6-di-O-pivaloyl-α-D-mannopyranoside. Acta Cryst C59:o184–o186
Renaudet O, Dumy P, Philouze C (2001) Methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-methoxyamino-α-D-glucopyranoside. Acta Cryst C57:309–310
Suresh CG, Ravindran B, Rao KN, Pathak T (2000) Comparison of the two anomers of methyl 2-(N-benzylamino)-2,3-dideoxy-4,6-O-phenylmethylene-3-C-phenylsulfonyl-D-glucopyranoside. Acta Cryst C56:1030–1032
Qiu ZZ, Hui XP, Xu PF (2005) 5-Phenyl-1,3,4-thiadiazol-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside. Acta Cryst C61:o475–o476
Low N, Garcia C, Melguizo M, Cobo J, Nogueras M, Sánchez A, López MD, Light ME (2001) A unique axially triacetylated xylopyranose structure, methyl 6-methoxy-2-methyl-1,3-dioxo-4- (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)amino -2,3-dihydro-1H-pyrrolo 3,4-c pyridine-7-carboxylate. Acta Cryst C57:222–224
Cheng ZH, Wu T, Bligh SWA, Bashall A, Yu BY (2004) cis-Eudesmane sesquiterpene glycosides from Liriope muscari and Ophiopogon japonicus. J Nat Prod 67:1761–1763
Eriksson L, Stenutz R, Widmalm G (2000) Methyl 4-O-β-L-fucopyranosyl α-D-glucopyranoside hemihydrate. Acta Cryst C56:702–704
Stenutz R, Shang M, Serianni S (1999) Methyl β-lactoside (methyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside) methanol solvate. Acta Cryst C55:1719–1721
Yokohama S, Miyazawa T, Litaka Y, Yamaizumi Z, Kasai H, Nishimura S (1979) Three-dimensional structure of hyper-modified nucleoside Q located in the wobbling position of tRNA. Nature 282:107–109
Seela F, Rosemeyer H, Melenewski A, Heithoff EM, Eickmeier H, Reuter H (2002) The α-D anomer of 5-aza-7-deaza-2′-deoxyguanosine. Acta Cryst C58:o142–o144
Marquez VE, Ezzitouni A, Russ P, Siddiqui MA, Ford H Jr, Feldman RJ, Mitsuya H, Goerge C, Barchi JJ Jr (1998) HIV-1 reverse transcriptase can discriminate between two conformationally locked carbocyclic AZT triphosphate analogues. J Am Chem Soc 120:2780–2789
Seela F, Chittepu P, He J, Eickmeier H (2004) 6-Aza-2′-deoxy-2′-arabinofluorouridine, a 2′-deoxyribonucleoside with an N-sugar conformation in the solid state and in solution. Acta Cryst C60:o884–o886
Seela F, Zhang Y, Xu K, Eickmeier H (2005) 7-Vinyl-8-aza-7-deaza-2′-deoxyadenosine monohydrate. Acta Cryst C61:o60–o062
Seela F, Xu K, Eickmeier H (2005) 2′-Deoxy-5-fluorotubercidin. Acta Cryst C61:o408–o410
Lin W, Xu K, Eickmeier H, Seela F (2005) 8-Aza-7-deaza-7-propynyladenosine methanol solvate. Acta Cryst C61:o195–o197
Seela F, Shaikh KI, Eickmeier H (2005) 7-Deaza-2′-deoxyguanosine. Acta Cryst C61:o151–o153
Seela F, Sirivolu VR, He J, Eickmeier H (2005) 3-Bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine: a nucleoside which strongly enhances DNA duplex stability. Acta Cryst C61:o67–o69
Lin W, Seela F, Eickmeier H, Reuter H (2004) N6-Etheno derivative of 7-deaza-2,8-diazaadenosine. Acta Cryst C60:o566–o568
Seela F, Shaikh KI, Eickmeier H (2004) 7-Deaza-2′-deoxy-7-propynylguanosine. Acta Cryst C60:o489–o491
Bats JW, Parsch J, Engels JW (2000) 1-Deoxy-1-(4-fluorophenyl)-β-D-ribofuranose, its hemihydrate, and 1-deoxy-1-(2,4-difluorophenyl)-β-D-ribofuranose: structural evidence for intermolecular C—H⋯F—C interactions. Acta Cryst C56:201–205
Seela F, Jawalekar AM, Eickmeier H (2004) 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-nitro-1H-indazole. Acta Cryst C60:o387–o389
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Brito-Arias, M. (2016). X-Ray Diffraction of Glycosides. In: Synthesis and Characterization of Glycosides. Springer, Cham. https://doi.org/10.1007/978-3-319-32310-7_9
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DOI: https://doi.org/10.1007/978-3-319-32310-7_9
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