Abstract
This paper reports application of the one-dimensional 13C NMR “extended” distortionless enhancement by polarization transfer (DEPT) editing method to the determination of hexopyranose ring 13C nuclei. Relative spatial arrangements of the vicinal protons in the local environment of a skeletal carbon atom are determined from the signs of intensity modulation profiles and connected with their specific positions in the ring. In combination with a computer simulation program, the “extended” DEPT sequence allows the straightforward and unambiguous assignment of the hexopyranose ring carbon atoms.
Keywords
Get full access to this article
View all access options for this article.
References
1.
Morris
G. A.
Freeman
R.
, J. Am. Chem. Soc. 101 , 760 (1979 ).
2.
Doddrell
D. M.
Pegg
D. T.
Bendall
M. R.
, J. Magn. Reson. 48 , 323 (1982 ).
3.
Pegg
D. T.
Doddrell
D. M.
Bendall
M. R.
, J. Chem. Phys. 77 , 2745 (1982 ).
4.
Wolfram
M. L.
Thompson
A.
, Methods Carbohydr. Chem. 2 , 211 (1963 ).
5.
Haworth
W. N.
, J. Chem. Soc. 107 , 8 (1915 ).
6.
Brobst
K. M.
, Methods Carbohydr. Chem. 6 , 3 (1972 ).
7.
Schenker
K. V.
Von Philipsborn
W.
, J. Magn. Reson. 61 , 294 (1985 ).
8.
Alam
T. M.
Assink
R. A.
Prabakar
S.
Loy
D. A.
, Magn. Reson. Chem. 34 , 603 (1996 );.
9.
Lux
P.
Brunet
F.
Virlet
J.
Cabane
B.
, Magn. Reson. Chem. 34 , 100 (1996 );.
10.
Lux
P.
Brunet
F.
Virlet
J.
Cabane
B.
, Magn. Reson. Chem. 34 , 173 (1996 );.
11.
Lux
P.
Brunet
F.
Desvaux
H.
Virlet
J.
, Magn. Reson. Chem. 31 , 623 (1993 );.
12.
Doddrell
D. M.
Pegg
D. T.
Bendall
M. R.
, J. Magn. Reson. 48 , 323 (1982 );.
13.
Helmer
B. J.
West
R.
, Organometallics 1 , 877 (1982 ).
14.
Pouységu
L.
Harket
M.
De Jéso
B.
Lartigue
J. C.
Pétraud
M.
Ratier
M.
, Magn. Reson. Chem. 35 , 735 (1997 ).
15.
Sweeley
C. C.
Bentley
R.
Makita
M.
Wells
W. W.
, J. Am. Chem. Soc. 85 , 2497 (1963 );.
16.
Chaplin
M. F.
Kennedy
J. F.
, Carbohydrate Analysis, a Practical Approach (Oxford , Washington DC , 1987 ), p. 1 .
17.
Helferich
B.
Zirner
J.
, Chem. Ber. 95 , 2604 (1962 );.
18.
Chittenden
G. J. F.
, Carbohydr. Res. 183 , 140 (1988 ).
19.
Deferrari
J. O.
Gros
E. G.
Mastronardi
I. O.
, Carbohydr. Res. 4 , 432 (1967 );.
20.
Deferrari
J. O.
Gros
E. G.
Thiel
I. M.
, Methods Carbohydr. Chem. 6 , 365 (1972 ).
21.
Koch
A.
Lamberth
C.
Wetterich
F.
Giese
B.
, Carbohydr. Res. 58 , 1083 (1993 ).
22.
Koeppen
B. H.
, Carbohydr. Res. 24 , 154 (1972 );.
23.
Takeo
K.
Kitamura
S.
Murata
Y.
, Carbohydr. Res. 224 , 111 (1992 ).
24.
Lartigue
J. C.
Pétraud
M.
Harket
M.
De Jéso
B.
Ratier
M.
, Comput. Chem. 20 , 219 (1996 ).
25.
Jakobsen
H. J.
Sørensen
U. B.
Bildsøe
H.
Sørensen
O. W.
, J. Magn. Reson. 63 , 601 (1985 );.
26.
Rastrup-Andersen
N.
Aagaard
G.
, Magn. Reson. Chem. 28 , 159 (1990 ).
27.
Kotowycz
G.
Lemieux
R. U.
, Chem. Rev. 73 , 669 (1973 );.
28.
Streefkerk
D. G.
De Bie
M. J. A.
Vliegenthart
J. F. G.
, Tetrahedron 29 , 883 (1973 ).
29.
Bock
K.
Pedersen
C.
, Adv. Carbohydr. Chem. Biochem. 41 , 27 (1983 ).