SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 130, Issue 36, 2008, Pages 11892-11900

13C-labeled N-acetyl-neuraminic acid in aqueous solution: Detection and quantification of acyclic keto, keto hydrate, and enol forms by 13C NMR spectroscopy

(3) Klepach, Thomas a Carmichael, Ian b Serianni, Anthony S a

a UNIVERSITY OF NOTRE DAME (United States)

b UNIVERSITY OF NOTRE DAME (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLUTIONS;

SOLUTIONS;

CARBON 13; DEUTERIUM; KETONE; N ACETYLNEURAMINIC ACID; CARBON; PYRAN DERIVATIVE; SIALIC ACID DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; ESTERIFICATION; ISOMER; PH; SOLVATION; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; SOLUTION AND SOLUBILITY;

CARBON ISOTOPES; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRANS; SIALIC ACIDS; SOLUTIONS; WATER;

EID: 51749096888 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja077565g Document Type: Article

Times cited : (42)

References (45)

1
- 0028829350
- Dwek, R. A.; Lellouch, A. C.; Wormald, M. R. J. Anat. 1995, 187, 279-292.
- (1995) J. Anat , vol.187 , pp. 279-292
- Dwek, R.A.¹ Lellouch, A.C.² Wormald, M.R.³

2
- 0031028909
- Wormald, M. R.; Rudd, P. M.; Harvey, D. J.; Chang, S.-C.; Scragg, I. G.; Dwek, R. A. Biochemistry 1997, 36, 1370-1380.
- (1997) Biochemistry , vol.36 , pp. 1370-1380
- Wormald, M.R.¹ Rudd, P.M.² Harvey, D.J.³ Chang, S.-C.⁴ Scragg, I.G.⁵ Dwek, R.A.⁶

3
- 31144449168
- Breton, C.; Snajdrova, L.; Jeanneau, C.; Koca, J.; Imberty, A. Glycobiology 2006, 16, 29R-37R.
- (2006) Glycobiology , vol.16
- Breton, C.¹ Snajdrova, L.² Jeanneau, C.³ Koca, J.⁴ Imberty, A.⁵

4
- 33746888249
- Kaneko, Y.; Nimmerjahn, F.; Ravetch, J. V. Science 2006, 313, 670-673.
- (2006) Science , vol.313 , pp. 670-673
- Kaneko, Y.¹ Nimmerjahn, F.² Ravetch, J.V.³

5
- 0036105953
- Maru, I.; Ohnishi, J.; Ohta, Y.; Tsukada, Y. J. Biosci. Bioeng. 2002, 93, 258-265.
- (2002) J. Biosci. Bioeng , vol.93 , pp. 258-265
- Maru, I.¹ Ohnishi, J.² Ohta, Y.³ Tsukada, Y.⁴

6
- 18844443684
- Tanner, M. E. Bioorg. Chem. 2005, 33, 216-228.
- (2005) Bioorg. Chem , vol.33 , pp. 216-228
- Tanner, M.E.¹

7
- 0001374704
- Maple, S. R.; Allerhand, A. J. Am. Chem. Soc. 1987, 109, 3168-3169.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 3168-3169
- Maple, S.R.¹ Allerhand, A.²

8
- 0032004124
- Drew, K. N.; Zajicek, J.; Bondo, G.; Bose, B.; Serianni, A. S. Carbohydr. Res. 1998, 307, 199-209.
- (1998) Carbohydr. Res , vol.307 , pp. 199-209
- Drew, K.N.¹ Zajicek, J.² Bondo, G.³ Bose, B.⁴ Serianni, A.S.⁵

9
- 0035929398
- Zhu, Y.; Zajicek, J.; Serianni, A. S. J. Org. Chem. 2001, 66, 6244-6251.
- (2001) J. Org. Chem , vol.66 , pp. 6244-6251
- Zhu, Y.¹ Zajicek, J.² Serianni, A.S.³

10
- 33847089740
- Czarniecki, M. F.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 8273-8279.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 8273-8279
- Czarniecki, M.F.¹ Thornton, E.R.²

11
- 0026863991
- Tropper, F. D.; Andersson, F. O.; Grand-Maitre, C.; Roy, R. Carbohydr. Res. 1992, 229, 149-154.
- (1992) Carbohydr. Res , vol.229 , pp. 149-154
- Tropper, F.D.¹ Andersson, F.O.² Grand-Maitre, C.³ Roy, R.⁴

12
- 51749104198
- Frisch, M. J.; et al. Gaussian03, Revision A.1; Gaussian, Inc., Pittsburgh, PA, 2003.
- Frisch, M. J.; et al. Gaussian03, Revision A.1; Gaussian, Inc., Pittsburgh, PA, 2003.

13
- 0000189651
- Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
- (1993) J. Chem. Phys , vol.98 , pp. 5648-5652
- Becke, A.D.¹

14
- 0347170005
- Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
- (1972) J. Chem. Phys , vol.56 , pp. 2257-2261
- Hehre, W.J.¹ Ditchfield, R.² Pople, J.A.³

15
- 0034641217
- Cloran, F.; Zhu, Y.; Osborn, J.; Carmichael, I.; Serianni, A. S. J. Am. Chem. Soc. 2000, 122, 6435-6448.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 6435-6448
- Cloran, F.¹ Zhu, Y.² Osborn, J.³ Carmichael, I.⁴ Serianni, A.S.⁵

16
- 0034827973
- Cloran, F.; Carmichael, I.; Serianni, A. S. J. Am. Chem. Soc. 2001, 123, 4781-4791.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 4781-4791
- Cloran, F.¹ Carmichael, I.² Serianni, A.S.³

17
- 0037039955
- Stenutz, R.; Carmichael, I.; Widmalm, G.; Serianni, A. S. J. Org. Chem. 2002, 67, 949-958.
- (2002) J. Org. Chem , vol.67 , pp. 949-958
- Stenutz, R.¹ Carmichael, I.² Widmalm, G.³ Serianni, A.S.⁴

18
- 0031209054
- Cancés, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
- (1997) J. Chem. Phys , vol.107 , pp. 3032
- Cancés, M.T.¹ Mennucci, B.² Tomasi, J.³

19
- 0033722017
- Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 5631.
- (2000) J. Phys. Chem. A , vol.104 , pp. 5631
- Cammi, R.¹ Mennucci, B.² Tomasi, J.³

20
- 0028300935
- 13C NMR spectra of 1 at pH 2 were referenced in this fashion.
- 13C NMR spectra of 1 at pH 2 were referenced in this fashion.

21
- 33847089740
- C1,H3eq couplings: Czarniecki, M.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 8273-8279;
- C1,H3eq couplings: Czarniecki, M.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 8273-8279;

22
- 0001434616
- Hori, H.; Nakajima, T.; Nishida, Y.; Ohrui, H.; Meguro, H. Tetrahedron Lett. 1988, 29, 6317-6320;
- (1988) Tetrahedron Lett , vol.29 , pp. 6317-6320
- Hori, H.¹ Nakajima, T.² Nishida, Y.³ Ohrui, H.⁴ Meguro, H.⁵

23
- 34250650911
- Májer, G.; Borbás, A.; Illyés, T. Z.; Szilágyi, L.; Bényei, A. C.; Lipták, A. Carbohydr. Res. 2007, 342, 1393-1404.
- (2007) Carbohydr. Res , vol.342 , pp. 1393-1404
- Májer, G.¹ Borbás, A.² Illyés, T.Z.³ Szilágyi, L.⁴ Bényei, A.C.⁵ Lipták, A.⁶

24
- 0011348982
- Edward, J. T. Chem. Ind. 1955, 1102.
- (1955) Chem. Ind , pp. 1102
- Edward, J.T.¹

25
- 0008954014
- de Mayo, P, Ed, Interscience Publishers: New York
- Lemieux, R. U. In Molecular Rearrangements; de Mayo, P., Ed.; Interscience Publishers: New York, 1964; p 709.
- (1964) Molecular Rearrangements , pp. 709
- Lemieux, R.U.¹

26
- 0004200453
- CRC Press: Boca Raton, FL
- Juaristi, E.; Cuevas, G. The Anomeric Effect; CRC Press: Boca Raton, FL, 1995.
- (1995) The Anomeric Effect
- Juaristi, E.¹ Cuevas, G.²

27
- 0018780599
- Serianni, A. S.; Pierce, J.; Barker, R. Biochemistry 1979, 18, 1192-1199.
- (1979) Biochemistry , vol.18 , pp. 1192-1199
- Serianni, A.S.¹ Pierce, J.² Barker, R.³

28
- 0026424307
- Vuorinen, T.; Serianni, A. S. Carbohydr. Res. 1990, 209, 13-31.
- (1990) Carbohydr. Res , vol.209 , pp. 13-31
- Vuorinen, T.¹ Serianni, A.S.²

29
- 0000405069
- Chiang, Y.; Kresge, A. J.; Pruszynski, P. J. Am. Chem. Soc. 1992, 114, 3103-3107.
- (1992) J. Am. Chem. Soc , vol.114 , pp. 3103-3107
- Chiang, Y.¹ Kresge, A.J.² Pruszynski, P.³

30
- 0000659605
- Greenzaid, P.; Luz, Z.; Samuel, D. J. Am. Chem. Soc. 1967, 89, 749-756.
- (1967) J. Am. Chem. Soc , vol.89 , pp. 749-756
- Greenzaid, P.¹ Luz, Z.² Samuel, D.³

31
- 51749122439
- Pocker, Y.; Meany, J. E.; Nist, B. J.; Zadorojny, C. J. Phys. Chem. 1969, 73, 2872-2882.
- (1969) J. Phys. Chem , vol.73 , pp. 2872-2882
- Pocker, Y.¹ Meany, J.E.² Nist, B.J.³ Zadorojny, C.⁴

32
- 0016663345
- Cooper, A. J. L.; Redfield, A. G. J, Biol. Chem. 1975, 250, 527-532.
- (1975) J, Biol. Chem , vol.250 , pp. 527-532
- Cooper, A.J.L.¹ Redfield, A.G.²

33
- 0001434616
- 1H NMR data showed significantly different (absolute) 2JC2,H3ax and 2J C2,H3eq values in 1αp (7.7 and 4.3 Hz, respectively, whereas nearly identical couplings were observed in 1βp (∼3.6 Hz, As reported previously for 3JC1,H3ax and 3J C1,H3eq (Hori, H, Nakajima, T, Nishida, Y, Ohrui, H, Meguro, H. Tetrahedron Lett. 1988, 29, 6317-6320, 2JC2,H3ax and 2J C2,H3eq can be used to distinguish between 1αp and 1βp see ref 34
- C2,H3eq can be used to distinguish between 1αp and 1βp (see ref 34).

34
- 0000892973
- Bock, K.; Pedersen, C. Acta Chem. Scand. 1977, B31, 354-358.
- (1977) Acta Chem. Scand , vol.B31 , pp. 354-358
- Bock, K.¹ Pedersen, C.²

35
- 51749092441
- C2,C3 = 44.0 Hz).
- C2,C3 = 44.0 Hz).

36
- 45249089910
- Klepach, T.; Zhang, W.; Carmichael, I.; Serianni, A. S. J. Org. Chem. 2008, 73, 4376-4387.
- (2008) J. Org. Chem , vol.73 , pp. 4376-4387
- Klepach, T.¹ Zhang, W.² Carmichael, I.³ Serianni, A.S.⁴

37
- 51749122913
- CCC values in unsaturated systems mimics that observed in saturated systems (Klepach, T.; Carmichael, I.; Serianni, A. S., unpublished results).
- CCC values in unsaturated systems mimics that observed in saturated systems (Klepach, T.; Carmichael, I.; Serianni, A. S., unpublished results).

38
- 33847802678
- Sojka, S. A.; Poranski, C. F., Jr.; Moniz, W. B. J. Am. Chem. Soc. 1975, 97, 5953-5955.
- (1975) J. Am. Chem. Soc , vol.97 , pp. 5953-5955
- Sojka, S.A.¹ Poranski Jr., C.F.² Moniz, W.B.³

39
- 51749115311
- a, and n were optimized simultaneously during the data fit using the Solver Routine in Microsoft Excel.
- a, and n were optimized simultaneously during the data fit using the Solver Routine in Microsoft Excel.

40
- 0000613049
- Serianni, A. S.; Pierce, J.; Huang, S.-G.; Barker, R. J. Am. Chem. Soc. 1982, 104, 4037.
- (1982) J. Am. Chem. Soc , vol.104 , pp. 4037
- Serianni, A.S.¹ Pierce, J.² Huang, S.-G.³ Barker, R.⁴

41
- 46149133747
- Fesik, S. W.; Kohlbrenner, W. E.; Gampe, Jr., R. T.; Olejniczak, E. T. Carbohydr. Res. 1986, 153, 136-140.
- (1986) Carbohydr. Res , vol.153 , pp. 136-140
- Fesik, S.W.¹ Kohlbrenner, W.E.² Gampe Jr., R.T.³ Olejniczak, E.T.⁴

42
- 0039226887
- Schmidt, H.; Friebolin, H. J. Carbohydr. Chem. 1983, 2, 405-413.
- (1983) J. Carbohydr. Chem , vol.2 , pp. 405-413
- Schmidt, H.¹ Friebolin, H.²

43
- 0026610494
- Ambrose, M. G.; Freese, S. J.; Reinhold, M. S.; Warner, T. G.; Vann, W. F. Biochemistry 1992, 31, 775-780.
- (1992) Biochemistry , vol.31 , pp. 775-780
- Ambrose, M.G.¹ Freese, S.J.² Reinhold, M.S.³ Warner, T.G.⁴ Vann, W.F.⁵

44
- 34547423743
- Azurmendi, H. F.; Vionnet, J.; Wrightson, L.; Trinh, L. B.; Shiloach, J.; Freedberg, D. I. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 11557-11561.
- (2007) Proc. Natl. Acad. Sci. U.S.A , vol.104 , pp. 11557-11561
- Azurmendi, H.F.¹ Vionnet, J.² Wrightson, L.³ Trinh, L.B.⁴ Shiloach, J.⁵ Freedberg, D.I.⁶

45
- 0000089343
- Larger disparities between calculated and experimental J-couplings are not considered to arise from inherent limitations of the DFT methodology but rather from simplifications and assumptions in the structural models used to calculate the couplings. In saccharides, the latter often involve the conformational properties of exocyclic OH groups, which can exert a major effect on both JCH and JCC values. Density functional theory with the B3LYP functional is known to produce accurate structural and energetic parameters in most organic molecules. This particular functional is specifically parametrized to reproduce accurate thermochemistry and matches closely results from high-level composite methods such as the Gaussian03 approach. Work in this laboratory and by other investigators has shown high agreement between B3LYP predictions of indirect nuclear spin-spin coupling constants and calculated couplings obtained by accurate high-level coupl
- CC (Cloran, F.; Carmichael, I.; Serianni, A. S. J. Phys. Chem. A 1999, 103, 3783-3795).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.