Abstract
Electrospray ionization tandem mass spectrometry was applied to the analysis of regiospecifically disubstituted β-cyclodextrins. Each disubstituted regioisomer showed unique fragmentation, distinguishing each of them unambiguously. These results demonstrate that mass spectrometry is the most straightforward method among those reported in the assignment of regioisomeric structures of these oligosaccharides.
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References
1.
(a)
Atwood
J.L.
Davies
J.E.D.
MacNicol
D.D.
Vögtle
F.
Lehn
J.-M.
, in Comprehensive Supramolecular Chemistry , Vol. 3 , Ed by
Szejtli
J.
Osa
T.
, Pergamon , Oxford, UK (1996 ); (b)
Easton
C.J.
Lincoln
S.F.
, Modified Cyclodextrins-Scaffolds and Templates for Supramolecular Chemistry. Imperial College Press , London, UK (1999 ).
2.
(a)
Rekharsky
M.V.
Yamamura
H.
Kawai
M.
Inoue
Y.
, J. Am. Chem. Soc. 123 , 5360 (2001 ). doi: 10.1021/ja003810j; (b)
Yamamura
H.
Rekharsky
M.V.
Ishihara
Y.
Kawai
M.
Inoue
Y.
, J. Am. Chem. Soc. 126 , 14224 (2004 ). doi: 10.1021/ja046612r
3.
(a)
Tabushi
I.
Kuroda
Y.
Yokota
K.
Yuan
L.C.
, J. Am. Chem. Soc. 103 , 711 (1981 ). doi: 10.1021/ja00393a056 ; (b)
Fujita
K.
Yamamura
H.
Matsunaga
A.
Imoto
T.
Mihashi
K.
Fujioka
T.
, J. Am. Chem. Soc. 108 , 4509 (1986 ). doi: 10.1021/ja00275a042 ; (c)
Atsumi
M.
Izumida
M.
Yuan
D.Q.
Fujita
K.
, Tetrahedron Lett. 41 , 8117 (2000 ). doi: 10.1016/S0040-4039(00)01415-5 ; (d)
Yamamura
H.
Iida
D.
Araki
S.
Kobayashi
K.
Katakai
R.
Kano
K.
Kawai
M.
, J. Chem. Soc. Perkin Trans. 1 21 , 3111 (1999 ). doi: 10.1039/a906436b ; (e)
Pearce
A.J.
Sinay
P.
, Angew. Chem. Int. Ed. Engl. 39 , 3610 (2000 ). doi: 10.1002/1521-3773(20001016)39:20<3610::AID-ANIE3610>3.0.CO;2V
4.
(a)
Fujita
K.
Matsunaga
A.
Imoto
T.
, Tetrahedron Lett. 25 , 5533 (1984 ). doi: 10.1016/S0040-4039(01)81618-X ; (b)
Fujita
K.
Yamamura
H.
Imoto
T.
, J. Org. Chem. 50 , 4393 (1984 ). doi: 10.1021/jo00222a042
5.
(a)
Yamamura
H.
Nagaoka
H.
Saito
K.
Kawai
M.
Butsugan
Y.
Nakajima
T.
Fujita
K.
, J. Org. Chem. 58 , 2936 (1993 ). doi: 10.1021/jo00063a005 ; (b)
Yuan
D.Q.
Koga
T.
Yamaguchi
M.
Fujita
K.
, J. Chem. Soc., Chem. Commun. 293 (1999 ). doi: 10.1021/ac980289r ; (c)
Yamamura
H.
Miyachi
S.
Kano
K.
Araki
S.
Lee
K.
Kawai
M.
Ueyama
N.
, Bull. Chem. Soc. Jpn 76 , 171 (2003 ). doi: 10.1246/bcsj.76.171
6.
(a)
Yang
Y.
Orlando
R.
, Anal. Chem. 68 , 570 (1996 ). doi: 10.1021/ac950932z ; (b)
Weiskopt
A.S.
Vouros
P.
Harvey
D.J.
, Anal. Chem. 70 , 4441 (1998 ). doi: 10.1021/ac980289r ; (c)
Cancilla
M.T.
Penn
S.G.
Lebrilla
C.B.
, Anal. Chem. 70 , 663 (1998 ). doi: 10.1021/ac9711100 ; (d)
Colangelo
J.
Orlando
R.
, Anal. Chem. 71 , 1479 (1999 ). doi: 10.1021/ac980980u ; (e)
Tseng
K.
Hedrick
J.L.
Lebrilla
C.B.
, Anal. Chem. 71 , 3745 (1999 ). doi: 10.1021/ac990095r
7.
Sforza
S.
Galaverna
G.
Corradini
R.
Dossena
A.
Marchelli
R.
, J. Am. Soc. Mass Spectrom. 14 , 124 (2003 ).
8.
Cucinotta
V.
D'Alessandro
F.
Impellizzeri
G.
Vecchio
G.
, Carbohydr. Res. 224 , 95 (1992 ). doi: 10.1016/0008-6215(92)84096-B
9.
(a)
Kanamori
K.
Kameda
E.
Kabetani
T.
Suemoto
T.
Okamoto
K.
Kaizaki
S.
, Bull. Chem. Soc. Jpn 68 , 2581 (1995 ); (b)
Iihara
H.
Nagata
T.
, Inorg. Chem. 37 , 4702 (1998 ). doi: 10.1021/ic971184u
10.
Domon
B.
Costello
C.E.
, Glycoconjugate J. 5 , 397 (1988 ).
11.
Icheln
D.
Gehrcke
B.
Baerbel
Y.
Mischnick
P.
Koenig
W.
Dessoy
M.A.
Morel
A.F.
, Carbohydr. Res. 280 , 237 (1996 ). doi: 10.1016/0008-6215(95)00322-3
12.
González
J.J.
Nieto
P.M.
Prados
P.
Ecgavarren
A.M.
de Mendoza
J.
, J. Org. Chem. 60 , 7419 (1995 ). doi: 10.1021/jo00128a012
13.
Li
T.
Kubota
M.
Okuda
S.
Hirano
T.
Ohashi
M.
, Eur. Mass Spectrom. 1 , 1 (1995 ).