The conformational behaviour of α,β-trehalose-like disaccharides and their C-glycosyl, imino-C-glycosyl and carbagalactose analogues depends on the chemical nature of the modification: an NMR investigation

Vı́ctor Garcı́a-Aparicio; Marı́a Del Carmen Fernández-Alonso; Jesús Angulo; Juan Luis Asensio; Fco. Javier Cañada; Jesús Jiménez-Barbero; David R. Mootoo; Xuhong Cheng

doi:10.1016/j.tetasy.2004.11.072

The conformational behaviour of α,β-trehalose-like disaccharides and their C-glycosyl, imino-C-glycosyl and carbagalactose analogues depends on the chemical nature of the modification: an NMR investigation

Vı́ctor Garcı́a-Aparicio, Marı́a Del Carmen Fernández-Alonso, Jesús Angulo, Juan Luis Asensio, Fco. Javier Cañada, Jesús Jiménez-Barbero, David R. Mootoo, Xuhong Cheng

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

The conformational behaviour of ß-O-Gal-(1?1)-a-Man 4 and the C-glycoside, carbaglycoside and aza-C-glycoside mimics 1–3 has been studied using J/NOE NMR data, molecular mechanics and molecular dynamics. It is shown that the population distributions around the glycosidic linkages of the different analogues depend on the chemical nature of the acetal or pseudoacetal residue.

Original language	English
Pages (from-to)	519-527
Number of pages	9
Journal	Tetrahedron: Asymmetry
Volume	16
Issue number	2
DOIs	https://doi.org/10.1016/j.tetasy.2004.11.072
Publication status	Published - 24 Jan 2005

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10.1016/j.tetasy.2004.11.072

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Garcı́a-Aparicio, V., Fernández-Alonso, M. D. C., Angulo, J., Asensio, J. L., Cañada, F. J., Jiménez-Barbero, J., Mootoo, D. R., & Cheng, X. (2005). The conformational behaviour of α,β-trehalose-like disaccharides and their C-glycosyl, imino-C-glycosyl and carbagalactose analogues depends on the chemical nature of the modification: an NMR investigation. Tetrahedron: Asymmetry, 16(2), 519-527. https://doi.org/10.1016/j.tetasy.2004.11.072

Garcı́a-Aparicio, Vı́ctor ; Fernández-Alonso, Marı́a Del Carmen ; Angulo, Jesús et al. / The conformational behaviour of α,β-trehalose-like disaccharides and their C-glycosyl, imino-C-glycosyl and carbagalactose analogues depends on the chemical nature of the modification: an NMR investigation. In: Tetrahedron: Asymmetry. 2005 ; Vol. 16, No. 2. pp. 519-527.

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title = "The conformational behaviour of α,β-trehalose-like disaccharides and their C-glycosyl, imino-C-glycosyl and carbagalactose analogues depends on the chemical nature of the modification: an NMR investigation",

abstract = "The conformational behaviour of {\ss}-O-Gal-(1?1)-a-Man 4 and the C-glycoside, carbaglycoside and aza-C-glycoside mimics 1–3 has been studied using J/NOE NMR data, molecular mechanics and molecular dynamics. It is shown that the population distributions around the glycosidic linkages of the different analogues depend on the chemical nature of the acetal or pseudoacetal residue.",

author = "V{\'ı}ctor Garc{\'ı}a-Aparicio and Fern{\'a}ndez-Alonso, {Mar{\'ı}a Del Carmen} and Jes{\'u}s Angulo and Asensio, {Juan Luis} and Ca{\~n}ada, {Fco. Javier} and Jes{\'u}s Jim{\'e}nez-Barbero and Mootoo, {David R.} and Xuhong Cheng",

year = "2005",

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day = "24",

doi = "10.1016/j.tetasy.2004.11.072",

language = "English",

volume = "16",

pages = "519--527",

journal = "Tetrahedron: Asymmetry",

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Garcı́a-Aparicio, V, Fernández-Alonso, MDC, Angulo, J, Asensio, JL, Cañada, FJ, Jiménez-Barbero, J, Mootoo, DR & Cheng, X 2005, 'The conformational behaviour of α,β-trehalose-like disaccharides and their C-glycosyl, imino-C-glycosyl and carbagalactose analogues depends on the chemical nature of the modification: an NMR investigation', Tetrahedron: Asymmetry, vol. 16, no. 2, pp. 519-527. https://doi.org/10.1016/j.tetasy.2004.11.072

The conformational behaviour of α,β-trehalose-like disaccharides and their C-glycosyl, imino-C-glycosyl and carbagalactose analogues depends on the chemical nature of the modification: an NMR investigation. / Garcı́a-Aparicio, Vı́ctor; Fernández-Alonso, Marı́a Del Carmen; Angulo, Jesús et al.
In: Tetrahedron: Asymmetry, Vol. 16, No. 2, 24.01.2005, p. 519-527.

Research output: Contribution to journal › Article › peer-review

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AU - Fernández-Alonso, Marı́a Del Carmen

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AB - The conformational behaviour of ß-O-Gal-(1?1)-a-Man 4 and the C-glycoside, carbaglycoside and aza-C-glycoside mimics 1–3 has been studied using J/NOE NMR data, molecular mechanics and molecular dynamics. It is shown that the population distributions around the glycosidic linkages of the different analogues depend on the chemical nature of the acetal or pseudoacetal residue.

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Garcı́a-Aparicio V, Fernández-Alonso MDC, Angulo J, Asensio JL, Cañada FJ, Jiménez-Barbero J et al. The conformational behaviour of α,β-trehalose-like disaccharides and their C-glycosyl, imino-C-glycosyl and carbagalactose analogues depends on the chemical nature of the modification: an NMR investigation. Tetrahedron: Asymmetry. 2005 Jan 24;16(2):519-527. doi: 10.1016/j.tetasy.2004.11.072