Synthesis and properties of septanose carbohydrates

Advances in Carbohydrate Chemistry and Biochemistry

Volumn 66, Issue 1, 2011, Pages 121-186

  Saha, Jaideep ^a   Peczuh, Mark W ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGLYCONE; ALKADIENE; ALKENE; ALKYNE; AZIDE; CARBENOID; DISACCHARIDE; GLUCOSE; GLYCOSIDE; HALOGEN; HEPTOSE; HYDROGEN SULFIDE; HYDROXYL GROUP; LECTIN; LITHIUM; MANNOSE; METHANOL; MOLYBDENUM; MONOSACCHARIDE; NUCLEOPHILE; NUCLEOTIDE; OLIGOMER; OLIGOSACCHARIDE; OXEPINE DERIVATIVE; PHENOL; PYRANOSIDE; SINGLE STRANDED RNA; SUGAR; THIOGLYCOSIDE; TRISACCHARIDE; PROTEIN;

ACETYLATION; ARTICLE; BIOCHEMISTRY; CALORIMETRY; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; CYCLOPROPANATION; DESILYLATION; DNA SYNTHESIS; EPIMERIZATION; EPOXIDATION; GLYCOSYLATION; HALOGENATION; HYDROGEN BOND; HYDROLYSIS; ISOMERIZATION; METHANOLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SIMMONS SMITH REACTION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE; TITRIMETRY; ANIMAL; CHEMISTRY; HUMAN; METABOLISM; METHODOLOGY; REVIEW;

ANIMALS; CARBOHYDRATE CONFORMATION; CHEMISTRY TECHNIQUES, SYNTHETIC; DISACCHARIDES; HUMANS; MONOSACCHARIDES; NUCLEOTIDES; PROTEINS;

EID: 84858757972     PISSN: 00652318     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-385518-3.00003-1     Document Type: Article

References (173)

1. S. L. Schreiber, Rethinking relationships between natural products, Nat. Chem. Biol., 3 (2007) 352.
2. A. T. Krueger, H. Lu, A. H. F. Lee, and E. T. Kool, Synthesis and properties of size-expanded DNAs: Toward designed, functional genetic systems, Acc. Chem. Res., 40 (2007) 141-150.
3. R. P. Cheng, S. H. Gellman, and W. F. DeGrado, β-Peptides: From structure to function, Chem. Rev., 101 (2001) 3219-3232.
4. S. H. Gellman, Foldamers: A manifesto, Acc. Chem. Res., 31 (1998) 173-180.
5. J. Gao, H. Liu, and E. T. Kool, Assembly of the complete eight-base artificial genetic helix, xDNA, and its interaction with the natural genetic system, Angew. Chem. Int. Ed., 44 (2005) 3118-3122.
6. A. H. F. Lee and E. T. Kool, A new four-base genetic helix, yDNA, composed of widened benzopyrimidine-purine pairs, J. Am. Chem. Soc., 127 (2005) 3332-3338.
7. H. Liu, J. Gao, and E. T. Kool, Helix-forming properties of size-expanded DNA, an alternative fourbase genetic form, J. Am. Chem. Soc., 127 (2005) 1396-1402.
8. H. Liu, J. Gao, and E. T. Kool, Size-expanded analogues of dG and dC: Synthesis and pairing properties in DNA, J. Org. Chem., 70 (2005) 639-647.
9. A. H. F. Lee and E. T. Kool, Novel benzopyrimidines as widened analogues of DNA bases, J. Org. Chem., 70 (2005) 132-140.
10. H. Lu, K. He, and E. T. Kool, yDNA: A new geometry for size-expanded base pairs, Angew. Chem. Int. Ed., 43 (2004) 5834-5836.
11. H. Liu, J. Gao, S. R. Lynch, Y. D. Saito, L. Maynard, and E. T. Kool, A four-base paired genetic helix with expanded size, Science, 302 (2003) 868-871.
12. A. R. Hernández and E. T. Kool, The components of xRNA: Synthesis and fluorescence of a full genetic set of size-expanded ribonucleosides, Org. Lett., 13 (2011) 676-679.
13. H. Lu, A. T. Krueger, J. Gao, H. Liu, and E. T. Kool, Toward a designed genetic system with biochemical function: Polymerase synthesis of single and multiple size-expanded DNA base pairs, Org. Biomol. Chem., 8 (2010) 2704-2710.
14. A. C. Gemperli, S. E. Rutledge, A. Maranda, and A. Schepartz, Paralog-selective ligands for Bcl-2 proteins, J. Am. Chem. Soc., 127 (2005) 1596-1597.
15. E. A. Harker and A. Schepartz, Cell-permeable β-peptide inhibitors of p53/hDM2 complexation, Chembiochem, 10 (2009) 990-993.
16. J. A. Kritzer, R. Zutshi, M. Cheah, F. A. Ran, R. Webman, T. M. Wongjirad, and A. Schepartz, Miniature protein inhibitors of the p53-hDM2 interaction, Chembiochem, 7 (2006) 29-31.
17. O. M. Stephens, S. Kim, B. D. Welch, M. E. Hodsdon, M. S. Kay, and A. Schepartz, Inhibiting HIV fusion with a β-peptide foldamer, J. Am. Chem. Soc., 127 (2005) 13126-13127.
18. Z. Pakulski, Seven membered ring sugars: A decade update, Pol. J. Chem., 80 (2006) 1293-1326.
19. Z. Pakulski, Seven membered ring sugars, Pol. J. Chem., 70 (1996) 667-707.
20. X. Chen and A. Varki, Advances in the biology and chemistry of sialic acids, ACS Chem. Biol., 5 (2010) 163-176.
21. C. Traving and R. Schauer, Structure, function and metabolism of sialic acids, Cell. Mol. Life Sci., 54 (1998) 1330-1349.
22. IUPAC-IUBMB Joint Commission on Biochemical Nomenclature (JCBN), Nomenclature of carbohydrates (Recommendations 1996), http://www.chem.qmul.ac.uk/iupac/2carb/.
23. Z. Pakulski and A. Zamojski, An efficient synthesis of 5-deoxy-D-ribohexose, Pol. J. Chem., 69 (1995) 912-917.
24. E. F. L. J. Anet, Degradation of carbohydrates. Part X. 2,3,4,5-Tetra-O-methyl-D-glucose, Carbohydr. Res., 8 (1968) 164-174.
25. S. D. Markad, S. M. Miller, M. Morton, and M. W. Peczuh, Hydroxyl group orientation affects hydrolysis rates of methyl [alpha]-septanosides, Tetrahedron Lett., 51 (2010) 1209-1212.
26. F. Moris-Varas, X.-H. Qian, and C.-H. Wong, Enzymatic/chemical synthesis and biological evaluation of seven-membered iminocyclitols, J. Am. Chem. Soc., 118 (1996) 7647-7652.
27. Q. Xinhua, F. Morís-Varas, and C.-H. Wong, Synthesis of C2-symmetrical polyhydroxyazepanes as inhibitors of glycosidases, Bioorg. Med. Chem. Lett., 6 (1996) 1117-1122.
28. J. C. Y. Wong, P. Lacombe, and C. F. Sturino, A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates, Tetrahedron Lett., 40 (1999) 8751-8754.
29. A. E. Stuetz and T. M. Wrodnigg, Imino sugars and glycosyl hydrolases: historical context, current aspects, emerging trends, Adv. Carbohydr. Chem. Biochem., 66 (2011) 187-298.
30. H. Li, Y. Blériot, C. Chantereau, J. M. Mallet, M. Sollogoub, Y. Zhang, E. Rodríguez-García, P. Vogel, J. Jiménez-Barbero, and P. Sinaÿ, The first synthesis of substituted azepanes mimicking monosaccharides: A new class of potent glycosidase inhibitors, Org. Biomol. Chem., 2 (2004) 1492-1499.
31. F. Marcelo, Y. He, S. A. Yuzwa, L. Nieto, J. Jimènez-Barbero, M. Sollogoub, D. J. Vocadlo, G. D. Davies, and Y. Blériot, Molecular basis for inhibition of GH84 glycoside hydrolases by substituted azepanes: Conformational flexibility enables probing of substrate distortion, J. Am. Chem. Soc., 131 (2009) 5390-5392.
32. M. L. Candenas, F. M. Pinto, C. G. Cintado, E. Q. Morales, I. Brouard, M. T. Diaz, M. Rico, E. Rodriguez, R. M. Rodriguez, R. Perez, R. L. Perez, and J. D. Martin, Synthesis and biological studies of flexible brevetoxin/ciguatoxin models with marked conformational preference, Tetrahedron, 58 (2002) 1921-1942.
33. F. Micheel and F. Sückfull, Eine neue Klasse von Zuckerderivaten, Justus Liebigs Ann. Chem., 502 (1933) 85-98.
34. F. Micheel and W. Spruck, Über eine weitere Dar-stellungsmethode für Zucker-Derivate mit siebengliedrigem Ringe (Septanosen), Ber. Dtsch. Chem. Ges. B, 67B (1934) 1665-1667.
35. J. D. Stevens, Large scale isolation of 1,2:3,4-di-O-isopropylidene-α-D-glucoseptanose and 2,3:4,5-di-O-isopropylidene-β-D-glucoseptanose, Carbohydr. Res., 346 (2011) 689-690.
36. T. Q. Tran and J. D. Stevens, Septanose carbohydrates. VII. Preparation of mono-O-isopropylidene derivatives of methyl β-D-glucoseptanoside and preparation of methyl α-L-idoseptanoside and its derivatives, Aust. J. Chem., 55 (2002) 171-178.
37. G. E. Driver and J. D. Stevens, Preparation of 1,2-O-isopropylidene derivatives of α-D-galactoseptanose, β-L-altroseptanose, and 3-O-methyl-a-D-guloseptanose, Carbohydr. Res., 334 (2001) 81-89.
38. C. J. Ng, D. C. Craig, and J. D. Stevens, Preparation of methyl β-idoseptanoside and its derivatives, Carbohydr. Res., 284 (1996) 249-263.
39. C. J. Ng and J. D. Stevens, Preparation of mono-O-isopropylidene derivatives of methyl α-D-glucoseptanoside, Carbohydr. Res., 284 (1996) 241-248.
40. G. E. Driver and J. D. Stevens, Septanose carbohydrates. III. Oxidation-reduction products from 1,2-3,4-di-O-isopropylidene-α-D-glucoseptanose: Preparation of L-idose derivatives, Aust. J. Chem., 43 (1990) 2063-2081.
41. C. J. Ng and J. D. Stevens, Methyl α-and β-D-glucoseptanosides, Methods Carbohydr. Chem., 7 (1976) 7-14.
42. J. D. Stevens, Septanose carbohydrates. I. Acid-catalysed reaction of D-glucose with acetone, Aust. J. Chem., 28 (1975) 525-557.
43. J. D. Stevens, Two septanose diacetals of D-glucose, J. Chem. Soc. D (1969) 1140-1141.
44. J. D. Stevens, Isolation of aldehydo and septanoside derivatives from the acid-catalyzed reaction of D-glucose and some of its derivatives with acetone-methanol, Carbohydr. Res., 21 (1972) 490-492.
45. J. C. McAuliffe and O. Hindsgaul, Use of acyclic glycosyl donors for furanoside synthesis, J. Org. Chem., 62 (1997) 1234-1239.
46. M. L. Wolfrom, D. I. Weisblat, and A. R. Hanze, The reactivity of the monothioacetals of glucose and galactose in relation to furanoside synthesis. I, J. Am. Chem. Soc., 66 (1944) 2065-2068.
47. M. L. Wolfrom, D. I. Weisblat, and A. R. Hanze, D-Glucose S-ethyl O-methyl monothioacetal, J. Am. Chem. Soc., 62 (1940) 3246-3250.
48. M. L. Wolfrom and D. I. Weisblat, Monothioacetals of galactose, J. Am. Chem. Soc., 62 (1940) 878-880.
49. J. C. McAuliffe and O. Hindsgaul, The synthesis of disaccharides terminating in D-septanosyl residues using acyclic intermediates, Synlett (1998) 307-309.
50. A. Köver, M. I. Matheu, Y. Díaz, and S. Castillón, A study of the oxepane synthesis by a 7-endo electrophile-induced cyclization reaction of alkenylsulfides. An approach towards the synthesis of septanosides, Arkivoc (2007) 364-379.
51. J. Saha and M. W. Peczuh, Access to ring-expanded analogues of 2-amino sugars, Org. Lett., 11 (2009) 4482-4484.
52. K. N. Kirschner and R. J. Woods, Solvent interactions determine carbohydrate conformation, Proc. Natl. Acad. Sci. U.S.A., 98 (2001) 10541-10545.
53. J. Saha and M. W. Peczuh, Expanding the scope of aminosugars: synthesis of 2-amino septanosyl glycoconjugates using septanosyl fluoride donors, Chem. Eur. J., 17 (2011) 7357-7365.
54. J. O. Hoberg and J. J. Bozell, Cyclopropanation and ring-expansion of unsaturated sugars, Tetrahedron Lett., 36 (1995) 6831-6834.
55. J. O. Hoberg, Formation of seven-membered oxacycles through ring expansion of cyclopropanated carbohydrates, J. Org. Chem., 62 (1997) 6615-6618.
56. R. Batchelor, J. E. Harvey, P. T. Northcote, P. Teesdale-Spittle, and J. O. Hoberg, Heptanosides from galactose-derived oxepenes via stereoselective addition reactions, J. Org. Chem., 74 (2009) 7627-7632.
57. C. V. Ramana, R. Murali, and M. Nagarajan, Synthesis and reactions of 1,2-cyclopropanated sugars, J. Org. Chem., 62 (1997) 7694-7703.
58. N. V. Ganesh and N. Jayaraman, Synthesis of septanosides through an oxyglycal route, J. Org. Chem., 72 (2007) 5500-5504.
59. G. S. Jones and W. J. Scott, Oxidative addition of palladium(0) to the anomeric center of carbohydrate electrophiles, J. Am. Chem. Soc., 114 (1992) 1491-1492.
60. O. Varela, G. M. de Fina, and R. M. de Lederkremer, The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide, stereoselective synthesis of α anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranosid-2-uloses, Carbohydr. Res., 167 (1987) 187-196.
61. N. V. Ganesh and N. Jayaraman, Synthesis of aryl, glycosyl, and azido septanosides through ring expansion of 1,2-cyclopropanated sugars, J. Org. Chem., 74 (2009) 739-746.
62. N. V. Ganesh, S. Raghothama, R. Sonti, and N. Jayaraman, Ring expansion of oxyglycals. Synthesis and conformational analysis of septanoside-containing trisaccharides, J. Org. Chem., 75 (2010) 215-218.
63. H. Ovaa, M. A. Leeuwenburgh, H. S. Overkleeft, G. A. van der Marel, and J. H. van Boom, An expeditious route to the synthesis of highly functionalized chiral oxepines from monosaccharides, Tetrahedron Lett., 39 (1998) 3025-3028.
64. M. W. Peczuh and N. L. Snyder, Carbohydrate-based oxepines: Ring expanded glycals for the synthesis of septanose saccharides, Tetrahedron Lett., 44 (2003) 4057-4061.
65. J. D. Rainier and S. P. Allwein, A highly efficient iterative approach to fused ether ring systems, Tetrahedron Lett., 39 (1998) 9601-9604.
66. E. J. Corey, M. C. Kang, M. C. Desai, A. K. Ghosh, and I. N. Houpis, Total synthesis of (±)-ginkgolide B, J. Am. Chem. Soc., 110 (1988) 649-651.
67. S. Castro and M. W. Peczuh, Sequential cyclization-elimination route to carbohydrate-based oxepines, J. Org. Chem., 70 (2005) 3312-3315.
68. E. Alcazar, J. M. Pletcher, and F. E. McDonald, Synthesis of seven-membered ring glycals via endoselective alkynol cyclo-isomerization, Org. Lett., 6 (2004) 3877-3880.
69. F. E. McDonald, Alkynol endo-cycloisomerizations and conceptually related transformations, Chem. Eur. J., 5 (1999) 3103-3106.
70. B. Koo and F. E. McDonald, Fischer carbene Catalysis of alkynol cycloisomerization: Application to the synthesis of the altromycin B disaccharide, Org. Lett., 9 (2007) 1737-1740.
71. S. Castro, C. S. Johnson, B. Surana, and M. W. Peczuh, An oxepinone route to carbohydrate based oxepines, Tetrahedron, 65 (2009) 7921-7926.
72. W. Pitsch, A. Russel, M. Zabel, and B. König, Synthesis of a functionalized cyclohepten-one from erythronic acid-4-lactone, Tetrahedron, 57 (2001) 2345-2347.
73. L. Alberch, G. Cheng, S.-K. Seo, X. Li, F. P. Boulineau, and A. Wei, Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides, J. Org. Chem., 76 (2011) 2532-2547.
74. G. Cheng, F. P. Boulineau, S.-T. Liew, Q. Shi, P. G. Wenthold, and A. Wei, Stereoselective epoxidation of 4-deoxypentenosides: A polarized-π model, Org. Lett., 8 (2006) 4545-4548.
75. A. M. Orendt, S. W. Roberts, and J. D. Rainier, The role of asynchronous bond formation in the diastereoselective epoxidation of cyclic enol ethers: A density functional theory study, J. Org. Chem., 71 (2006) 5565-5573.
76. S. D. Markad, S. Xia, N. L. Snyder, B. Surana, M. D. Morton, C. M. Hadad, and M. W. Peczuh, Stereoselectivity in the epoxidation of carbohydrate-based oxepines, J. Org. Chem., 73 (2008) 6341-6354.
77. W. S. Fyvie, M. Morton, and M. W. Peczuh, Synthesis of 2-iodo-2-deoxy septanosides from a D-xylose-based oxepine: Intramolecular cyclization in the absence of a glycosyl acceptor, Carbohydr. Res., 339 (2004) 2363-2370.
78. M. W. Peczuh, N. L. Snyder, and W. S. Fyvie, Synthesis, crystal structure, and reactivity of a D-xylose based oxepine, Carbohydr. Res., 339 (2004) 1163-1171.
79. F. P. Boulineau and A. Wei, Synthesis of l-sugars from 4-deoxypentenosides, Org. Lett., 4 (2002) 2281-2283.
80. M. A. Boone, F. E. McDonald, J. Lichter, S. Lutz, R. Cao, and K. I. Hardcastle, 1,5-α-D-Mannoseptanosides, ring-size isomers that are impervious to a-mannosidase-catalyzed hydrolysis, Org. Lett., 11 (2009) 851-854.
81. S. Castro, W. S. Fyvie, S. A. Hatcher, and M. W. Peczuh, Synthesis of a-D-idoseptanosyl glycosides using an S-phenyl septanoside donor, Org. Lett., 7 (2005) 4709-4712.
82. H. M. I. Osborn and A. Turkson, Synthesis and NMR spectroscopic analysis of 3-nitro-pyranoside, 3-nitro-septanoside and 4-nitro-septanoside derivatives by condensation of the anion of nitromethane with glycoside dialdehydes, Tetrahedron: Asymmetry, 20 (2009) 2162-2166.
83. M. L. Wolfrom, U. G. Nayak, and T. Radford, A novel reaction of a nitro sugar with alcohols, Proc. Natl. Acad. Sci. U.S.A., 58 (1967) 1848-1851.
84. M. E. Butcher, J. C. Ireson, J. B. Lee, and M. J. Tyler, Seven and eight membered ring sugars and related systems: The synthesis of some septanose rings from dioxepans, Tetrahedron, 33 (1977) 1501-1507.
85. M. E. Butcher and J. B. Lee, Seven-membered ring sugars: factors influencing the formation of branched-chain 3-deoxy-3-nitro-septanosides, J. Chem. Soc., Chem. Commun. (1974) 1010-1011.
86. K. C. Nicolaou, H. J. Mitchell, F. L. van Delft, F. Rübsam, and R. M. Rodríguez, Expeditious routes to evernitrose and vancosamine derivatives and synthesis of a model vancomycin aryl glycoside, Angew. Chem. Int. Ed., 37 (1998) 1871-1874.
87. D. E. Wright, The orthosomycins, a new family of antibiotics, Tetrahedron, 35 (1979) 1207-1237.
88. K. Sato and J. Yoshimura, Branched-chain sugars. XII. The stereoselectivities in the reaction of methyl 4,6-O-benzylidene-α-and-β-D-hexopyranosid-3-uloses with diazomethane, Bull. Chem. Soc. Jpn., 51 (1978) 2116-2121.
89. B. Flaherty, S. Nahar, W. G. Overend, and N. R. Williams, Branched-chain sugars. XIV. Reactions of glycosulose derivatives with diazomethane. Ring expansion of glycosulose derivatives, J. Chem. Soc., Perkin Trans. 1 (1973) 632-638.
90. B. Flaherty, W. G. Overend, and N. R. Williams, Ring expansion of a glycoside, J. Chem. Soc., Chem. Commun. (1966) 434-436.
91. R. L. Whistler and C. S. Campbell, Synthesis of septanose derivatives of 6-thio-D-galactose, J. Org. Chem., 31 (1966) 816-818.
92. R. Batchelor, J. E. Harvey, P. Teesdale-Spittle, and J. O. Hoberg, Mechanistic studies of rearrangements during the ring expansions of cyclopropanated carbohydrates, Tetrahedron Lett., 50 (2009) 7283-7285.
93. Y. Le Merrer, M. Fuzier, I. Dosbaa, M.-J. Foglietti, and J.-C. Depezay, Synthesis of thiosugars as weak inhibitors of glycosidases, Tetrahedron, 53 (1997) 16731-16746.
94. M. Fuzier, Y. Le Merrer, and J.-C. Depezay, Thiosugars from D-mannitol, Tetrahedron Lett., 36 (1995) 6443-6446.
95. V. Spiwok, B. Králová, and I. Tvaroška, Modelling of β-D-glucopyranose ring distortion in different force fields: a metadynamics study, Carbohydr. Res., 345 (2010) 530-537.
96. G. Favini, Conformational analysis of seven-membered cyclic systems, THEOCHEM, 93 (1983) 139-152.
97. D. F. Bocian and H. L. Strauss, Conformational structure and energy of cycloheptane and some related oxepanes, J. Am. Chem. Soc., 99 (1977) 2876-2882.
98. J. B. Hendrickson, Molecular geometry. VII. Modes of interconversion in the medium rings, J. Am. Chem. Soc., 89 (1967) 7047-7061.
99. J. B. Hendrickson, Molecular geometry. VI. Methyl-substituted cycloalkanes, J. Am. Chem. Soc., 89 (1967) 7043-7046.
100. D. F. Bocian, H. M. Pickett, T. C. Rounds, and H. L. Strauss, Conformations of cycloheptane, J. Am. Chem. Soc., 97 (1975) 687-695.
101. A. Espinosa, M. A. Gallo, A. Entrena, and J. A. Gómez, Theoretical conformational analysis of sevenmembered rings. V. MM2 and MM3 study of oxepane, J. Mol. Struct., 323 (1994) 247-256.
102. A. Entrena, J. Campos, J. A. Gómez, M. A. Gallo, and A. Espinosa, A new systematization of the conformational behavior of seven-membered rings. Isoclinal anomeric and related orientations. 1, J. Org. Chem., 62 (1997) 337-349.
103. A. Espinosa, A. Entrena, M. A. Gallo, J. Campos, J. F. Dominguez, E. Camacho, and R. Garrido, Conformational analysis of some 1,4-dioxepane systems. 2. Methoxy-1,4-dioxepanes, J. Org. Chem., 55 (1990) 6018-6023.
104. J. F. Stoddart and W. A. Szarek, Conformational studies on 1,3-dioxepans. Part III. 2,5-O-methylene-D-mannitol and some related compounds, J. Chem. Soc. B (1971) 437-442.
105. J. F. Stoddart, Stereochemistry of Carbohydrates (1971) Wiley & Sons, New York.
106. J. B. Hendrickson, Molecular geometry. IV. The medium rings, J. Am. Chem. Soc., 86 (1964) 4854-4866.
107. C. Altona and M. Sundaralingam, Conformational analysis of the sugar ring in nucleosides and nucleotides. New description using the concept of pseudorotation, J. Am. Chem. Soc., 94 (1972) 8205-8212.
108. D. Cremer and J. A. Pople, General definition of ring puckering coordinates, J. Am. Chem. Soc., 97 (1975) 1354-1358.
109. G.R. J. Thatcher, (Ed.), In The Anomeric Effect and Associated Stereoelectronic Effects, American Chemical Society, Washington, DC, 1993.
110. P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, (1983) Wiley, New York.
111. W. A. Szarek, and D. Horton, (Eds.) In Anomeric Effect: Origins and Consequences, ACS Symp. Ser., Vol. 87, pp. 1-127.
112. A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, (1983) Springer Verlag, New York.
113. S. Desilets and M. St. Jacques, The anomeric effect in thio derivatives of benzocycloheptene, Can. J. Chem., 70 (1992) 2650-2658.
114. S. Desilets and M. St. Jacques, Anomeric effect in seven-membered rings: A conformational study of 2-oxa derivatives of benzocycloheptene by NMR, J. Am. Chem. Soc., 109 (1987) 1641-1648.
115. H. Booth, K. A. Khedhair, and S. A. Readshaw, Experimental studies of the anomeric effect: Part I. 2-substituted tetrahydropyrans, Tetrahedron, 43 (1987) 4699-4723.
116. H. Booth, J. Mark Dixon, and R. Simon, Experimental studies of the anomeric effect. Part V. The influence of some solvents on the conformational equilibria in 2-methoxy- and 2-(2',2',2'-trifluoroethoxy)-tetrahydropyran, Tetrahedron, 48 (1992) 6151-6160.
117. U. Salzner and P.v.R. Schleyer, Ab initio examination of anomeric effects in tetrahydropyrans, 1,3-dioxanes, and glucose, J. Org. Chem., 59 (1994) 2138-2155.
118. C. B. Anderson and D. T. Sepp, Conformation and the anomeric effect in 2-halotetrahydropyrans, J. Org. Chem., 32 (1967) 607-611.
119. J.-P. Praly and R. U. Lemieux, Influence of solvent on the magnitude of the anomeric effect, Can. J. Chem., 65 (1987) 213-223.
120. R. U. Lemieux, A. A. Pavia, J. C. Martin, and K. A. Watanabe, Solvation effects on conformational equilibria. Studies related to the conformational properties of 2-methoxytetrahydropyran and related methyl glycopyranosides, Can. J. Chem., 47 (1969) 4427-4439.
121. C. Mayato, R. Dorta, and J. Vázquez, Experimental evidence on the hydroxymethyl group conformation in alkyl β-D-mannopyranosides, Tetrahedron: Asymmetry, 15 (2004) 2385-2397.
122. M. Kraszni, Z. Szakács, and B. Noszál, Determination of rotamer populations and related parameters from NMR coupling constants: A critical review, Anal. Bioanal. Chem., 378 (2004) 1449-1463.
123. R. Stenutz, I. Carmichael, G. Widmalm, and A. S. Serianni, Hydroxymethyl group conformation in saccharides: Structural dependencies of 2JHH, 3JHH, and 1JCH spin-spin coupling constants, J. Org. Chem., 67 (2002) 949-958.
124. C. Nóbrega and J. T. Vázquez, Conformational study of the hydroxymethyl group in α-D-mannose derivatives, Tetrahedron: Asymmetry, 14 (2003) 2793-2801.
125. M. P. DeMatteo, N. L. Snyder, M. Morton, D. M. Baldisseri, C. M. Hadad, and M. W. Peczuh, Septanose carbohydrates: Synthesis and conformational studies of methyl α-D-glycero-D-idoseptanoside and methyl β-D-glycero-D-guloseptanoside, J. Org. Chem., 70 (2005) 24-38.
126. M. P. DeMatteo, S. Mei, R. Fenton, M. Morton, D. M. Baldisseri, C. M. Hadad, and M. W. Peczuh, Conformational analysis of methyl 5-O-methyl septanosides: effect of glycosylation on conformer populations, Carbohydr. Res., 341 (2006) 2927-2945.
127. V. A. Danilova, N. V. Istomina, and L. B. Krivdin, 13C-13C Spin-spin coupling constants in structural studies: XXXVII. Rotational conformations of hydroxy groups in pyranose, furanose, and septanose rings, Russ. J. Org. Chem., 40 (2004) 1194-1199.
128. M. R. Duff, Jr., W. S. Fyvie, S. D. Markad, A. E. Frankel, C. V. Kumar, J. A. Gascón, and M. W. Peczuh, Computational and experimental investigations of mono-septanoside binding by Concanavalin A: Correlation of ligand stereochemistry to enthalpies of binding, Org. Biomol. Chem., 9 (2011) 154-164.
129. J. B. Houseknecht, P. R. McCarren, T. L. Lowary, and C. M. Hadad, Conformational studies of methyl 3-O-methyl-α-D-arabinofuranoside: An approach for studying the conformation of furanose rings, J. Am. Chem. Soc., 123 (2001) 8811-8824.
130. V. A. Danilova and L. B. Krivdin, 13C-13C spin-spin coupling constants in structural studies: XXXVI. Stereochemical study of the septanose ring, Russ. J. Org. Chem., 40 (2004) 57-62.
131. S. Castro, M. Duff, N. L. Snyder, M. Morton, C. V. Kumar, and M. W. Peczuh, Recognition of septanose carbohydrates by concanavalin A, Org. Biomol. Chem., 3 (2005) 3869-3872.
132. A. A. Koshkin, P. Nielsen, M. Meldgaard, V. K. Rajwanshi, S. K. Singh, and J. Wengel, LNA (locked nucleic acid): An RNA mimic forming exceedingly stable LNA:LNA duplexes, J. Am. Chem. Soc., 120 (1998) 13252-13253.
133. V. K. Rajwanshi, A. E. Hakansson, M. D. Sorensen, S. Pitsch, S. K. Singh, R. Kumar, P. Nielsen, and J. Wengel, The eight stereoisomers of LNA (Locked nucleic acid): A remarkable family of strong RNA binding molecules, Angew. Chem. Int. Ed., 39 (2000) 1656-1659.
134. S. Hildbrand and C. Leumann, Enhancing DNA triple helix stability at neutral pH by the use of oligonucleotides containing a more basic deoxycytidine analog, Angew. Chem. Int. Ed., 35 (1996) 1968-1970.
135. R. Steffens and C. J. Leumann, Synthesis and thermodynamic and biophysical properties of tricyclo-DNA, J. Am. Chem. Soc., 121 (1999) 3249-3255.
136. S. Tripathi, B. G. Roy, M. G. B. Drew, B. Achari, and S. B. Mandal, Synthesis of oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosides from D-glucose: A cycloaddition approach, J. Org. Chem., 72 (2007) 7427-7430.
137. A. Kittaka, T. Asakura, T. Kuze, H. Tanaka, N. Yamada, K. T. Nakamura, and T. Miyasaka, Cyclization reactions of nucleoside anomeric radical with olefin tethered on base: Factors that induce anomeric stereochemistry, J. Org. Chem., 64 (1999) 7081-7093.
138. B. R. Babu, L. Keinicke, M. Petersen, C. Nielsen, and J. Wengel, 2'-Spiro ribo- and arabinonucleosides: Synthesis, molecular modelling and incorporation into oligodeoxynucleotides, Org. Biomol. Chem., 1 (2003) 3514-3526.
139. S. Z. Dong and L. A. Paquette, Stereoselective synthesis of conformationally constrained 2'-deoxy-4'-thia beta-anomeric spirocyclic nucleosides featuring either hydroxyl configuration at C5', J. Org. Chem., 70 (2005) 1580-1596.
140. R. Hartung and L. A. Paquette, Practical synthesis of enantiopure spiro 4.4 nonane C-(2'-deoxy) ribonucleosides, J. Org. Chem., 70 (2005) 1597-1604.
141. L. A. Paquette and S. Z. Dong, Stereoselective synthesis of beta-anomeric 4'-thiaspirocyclic ribonucleosides carrying the full complement of RNA-level hydroxyl substitution, J. Org. Chem., 70 (2005) 5655-5664.
142. A. Roy, B. Achari, and S. B. Mandal, An easy access to spiroannulated glyco-oxetane, -thietane and -azetane rings: Synthesis of spironucleosides, Tetrahedron Lett., 47 (2006) 3875-3879.
143. S. Sahabuddin, A. Roy, M. G. B. Drew, B. G. Roy, B. Achari, and S. B. Mandal, Sequential ringclosing metathesis and nitrone cycloaddition on glucose-derived substrates: A divergent approach to analogues of spiroannulated carbanucleosides and conformationally locked nucleosides, J. Org. Chem., 71 (2006) 5980-5992.
144. A. Eschenmoser, Searching for nucleic acid alternatives, Chimia, 59 (2005) 836-850.
145. M. O. Ebert, A. Luther, H. K. Huynh, R. Krishnamurthy, A. Eschenmoser, and B. Jaun, NMR solution structure of the duplex formed by self-pairing of α-L-arabinopyranosyl-(4',2')-(CGAATTCG), Helv. Chim. Acta, 85 (2002) 4055-4073.
146. A. Eschenmoser and R. Krishnamurthy, Chemical etiology of nucleic acid structure, Pure Appl. Chem., 72 (2000) 343-345.
147. K. U. Schoning, P. Scholz, S. Guntha, X. Wu, R. Krishnamurthy, and A. Eschenmoser, Chemical etiology of nucleic acid structure: The α-threofuranosyl-(3',2') oligonucleotide system, Science, 290 (2000) 1347-1351.
148. S. Pitsch, S. Wendeborn, R. Krishnamurthy, A. Holzner, M. Minton, M. Bolli, C. Miculca, N. Windhab, R. Micura, M. Stanek, B. Jaun, and A. Eschenmoser, Pentopyranosyl oligonucleotide systems. 9th Communication, Helv. Chim. Acta, 86 (2003) 4270-4363.
149. M. Egli, P. S. Pallan, R. Pattanayek, C. J. Wilds, P. Lubini, G. Minasov, M. Dobler, C. J. Leumann, and A. Eschenmoser, Crystal structure of homo-DNA and Nature's choice of pentose over hexose in the genetic system, J. Am. Chem. Soc., 128 (2006) 10847-10856.
150. G. Sizun, D. Dukhan, J. F. Griffon, L. Griffe, J. C. Meillon, F. Leroy, R. Storer, J. P. Sommadossi, and G. Gosselin, Synthesis of the first example of a nucleoside analogue bearing a 5'-deoxy-β-D-alloseptanose as a seven-membered ring sugar moiety, Carbohydr. Res., 344 (2009) 448-453.
151. D. Sabatino and M. J. Damha, Oxepane nucleic acids: Synthesis, characterization, and properties of oligonucleotides bearing a seven-membered carbohydrate ring, J. Am. Chem. Soc., 129 (2007) 8259-8270.
152. M. Nomura, K. Endo, S. Shuto, and A. Matsuda, Nucleosides and nucleotides. 191. Ring expansion reaction of 1-[2,3,5-tri-O-TBS-4 alpha-formyl-beta-D-ribo-pentofuranosyl] uracil by treating with (methylene)triphenylphosphorane to give a new nucleoside containing dihydrooxepine ring at the sugar moiety, Tetrahedron, 55 (1999) 14847-14854.
153. M. Nomura, S. Shuto, M. Tanaka, T. Sasaki, S. Mori, S. Shigeta, and A. Matsuda, Nucleosides and Nucleotides. 185. Synthesis and biological activities of 4'-α-C-branched-chain sugar pyrimidine nucleosides, J. Med. Chem., 42 (1999) 2901-2908.
154. A. Bhattacharjee, S. Datta, P. Chattopadhyay, N. Ghoshal, A. P. Kundu, A. Pal, R. Mukhopadhyay, S. Chowdhury, A. Bhattacharjya, and A. Patra, Synthesis of chiral oxepanes and pyrans by 3-O-allylcarbohydrate nitrone cycloaddition (3-OACNC), Tetrahedron, 59 (2003) 4623-4639.
155. D. Sabatino and M. J. Damha, Synthesis and properties of oligonucleotides containing a 7-membered (oxepane) sugar ring, Nucleosides Nucleotides, 26 (2007) 1185-1188.
156. B. Bennuaskalmowski, K. Krolikiewicz, and H. Vorbruggen, A new simple nucleoside synthesis, Tetrahedron Lett., 36 (1995) 7845-7848.
157. A. De Mesmaeker, R. Haener, P. Martin, and H. E. Moser, Antisense oligonucleotides, Acc. Chem. Res., 28 (1995) 366-374.
158. E. Uhlmann and A. Peyman, Antisense oligonucleotides: A new therapeutic principle, Chem. Rev., 90 (1990) 543-584.
159. M. M. Mangos, K. L. Min, E. Viazovkina, A. Galarneau, M. I. Elzagheid, M. A. Parniak, and M. J. Damha, Efficient RNase H-directed cleavage of RNA promoted by antisense DNA or 2' F-ANA constructs containing acyclic nucleotide inserts, J. Am. Chem. Soc., 125 (2003) 654-661.
160. A. Gelbin, B. Schneider, L. Clowney, S. H. Hsieh, W. K. Olson, and H. M. Berman, Geometric parameters in nucleic acids: Sugar and phosphate constituents, J. Am. Chem. Soc., 118 (1996) 519-529.
161. A. Noy, A. Perez, M. Marquez, F. J. Luque, and M. Orozco, Structure, recognition properties, and flexibility of the DNA-RNA hybrid, J. Am. Chem. Soc., 127 (2005) 4910-4920.
162. M. J. Damha, C. J. Wilds, A. Noronha, I. Brukner, G. Borkow, D. Arion, and M. A. Parniak, Hybrids of RNA and arabinonucleic acids (ANA and 2' F-ANA) are substrates of ribonuclease H, J. Am. Chem. Soc., 120 (1998) 12976-12977.
163. P. Nielsen, H. M. Pfundheller, and J. Wengel, A novel class of conformationally restricted oligonucleotide analogues: Synthesis of 2',3'-bridged monomers and RNA-selective hybridisation, Chem. Commun. (1997) 825-826.
164. J. Li and R. M. Wartell, RNase H1 can catalyze RNA/DNA hybrid formation and cleavage with stable hairpin or duplex DNA oligomers, Biochemistry, 37 (1998) 5154-5161.
165. Y. Oda, S. Iwai, E. Ohtsuka, M. Ishikawa, M. Ikehara, and H. Nakamura, Binding of nucleic acids to E. coli RNase HI observed by NMR and CD spectroscopy, Nucleic Acids Res., 21 (1993) 4690-4695.
166. A. Tauss, A. J. Steiner, A. E. Stütz, C. A. Tarling, S. G. Withers, and T. M. Wrodnigg, l-Idoseptanosides: substrates of D-glucosidases?Tetrahedron: Asymmetry, 17 (2006) 234-239.
167. Y. Li, D. Horton, V. Barberousse, F. Bellamy, P. Renaut, and S. Samreth, Chemical interconversions of 4-cyanophenyl 1,5-dithio-β-D-xylopyranoside (Beciparcil): Structural modification at the C-4 position, Carbohydr. Res., 314 (1998) 161-167.
168. F. Bellamy, D. Horton, J. Millet, F. Picart, S. Samreth, and J. B. Chazan, Glycosylated derivatives of benzophenone, benzhydrol and benzhydril as potential venous antithrombotic agents, J. Med. Chem., 36 (1993) 898-903.
169. E. Bozó, A. Medgyes, S. Boros, and J. Kuszmann, Synthesis of 4-substituted phenyl 2,5-anhydro-1,6-dithio-α-gluco-and-α-guloseptanosides possessing antithrombotic activity, Carbohydr. Res., 329 (2000) 25-40.
170. E. Bozó, S. Boros, L. Párkányi, and J. Kuszmann, Synthesis of 4-cyano- and 4-nitrophenyl 2,5-anhydro-1,6-dithio-α-D-gluco-and-α-L-guloseptanosides carrying different substituents at C-3 and C-4, Carbohydr. Res., 329 (2000) 269-286.
171. E. Bozó, T. Gáti, Á. Demeter, and J. Kuszmann, Synthesis of 4-cyano and 4-nitrophenyl 1,6-dithio-manno-, -ido- and -glucoseptanosides possessing antithrombotic activity, Carbohydr. Res., 337 (2002) 1351-1365.
172. D. Berger, L. E. Overman, and P. A. Renhowe, Total synthesis of (+)-isolaurepinnacin. Use of acetalalkene cyclizations to prepare highly functionalized seven-membered cyclic ethers, J. Am. Chem. Soc., 119 (1997) 2446-2452.
173. S. Basu, B. Ellinger, S. Rizzo, C.l. Deraeve, M. Schürmann, H. Preut, H.-D. Arndt, and H. Waldmann, Biology-oriented synthesis of a natural-product inspired oxepane. Collection yields a small-molecule activator of the Wnt-pathway, Proc. Natl. Acad. Sci. USA., 108 (2011) 6805-6810.