Methyl tetra-O-acetyl-α-d-glucopyranuronate: crystal structure and influence on the crystallisation of the β anomer

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dc.contributor.authorHayes, John A.
dc.contributor.authorEccles, Kevin S.
dc.contributor.authorLawrence, Simon E.
dc.contributor.authorMoynihan, Humphrey A.
dc.contributor.funderIrish Research Council for Science Engineering and Technologyen
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderUniversity College Cork
dc.date.accessioned2016-07-25T10:27:09Z
dc.date.available2016-07-25T10:27:09Z
dc.date.issued2016-03-14
dc.date.updated2016-07-22T15:33:48Z
dc.description.abstractMethyl tetra-O-acetyl-β-d-glucopyranuronate (1) and methyl tetra-O-acetyl-α-d-glucopyranuronate (3) were isolated as crystalline solids and their crystal structures were obtained. That of the β anomer (1) was the same as that reported by Root et al., while anomer (3) was found to crystallise in the orthorhombic space group P212121 with two independent molecules in the asymmetric unit. No other crystal forms were found for either compound upon recrystallisation from a range of solvents. The α anomer (3) was found to be an impurity in initially precipitated batches of β-anomer (1) in quantities <3%; however, it was possible to remove the α impurity either by recrystallisation or by efficient washing, i.e. the α anomer is not incorporated inside the β anomer crystals. The β anomer (1) was found to grow as prisms or needles elongated in the a crystallographic direction in the absence of the α impurity, while the presence of the α anomer (3) enhanced this elongation.en
dc.description.sponsorshipScience Foundation Ireland (Grant Numbers 07/SRC/B1158; 05/PICA/B802/EC07; 12/RC/2275); Irish Research Council for Science Engineering and Technology (PD/2012/2652); University College Cork (2013 Strategic Research Fund)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationHayes, J.A., Eccles, K.S., Lawrence, S.E. and Moynihan, H.A. (2016) ‘Methyl tetra-O-acetyl-α-d-glucopyranuronate: crystal structure and influence on the crystallisation of the β anomer’, Carbohydrate Research, 425, pp. 35-39. doi:10.1016/j.carres.2016.01.012en
dc.identifier.doi10.1016/j.carres.2016.01.012
dc.identifier.endpage39en
dc.identifier.issn0008-6215
dc.identifier.journaltitleCarbohydrate Researchen
dc.identifier.startpage35en
dc.identifier.urihttps://hdl.handle.net/10468/2934
dc.identifier.volume425en
dc.language.isoenen
dc.publisherElsevier Ltden
dc.rights© 2016 Elsevier Ltd. All rights reserved. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.subjectMethyl tetra-O-acetyl-d-glucopyranuronateen
dc.subjectCrystallisation of anomersen
dc.titleMethyl tetra-O-acetyl-α-d-glucopyranuronate: crystal structure and influence on the crystallisation of the β anomeren
dc.typeArticle (peer-reviewed)en
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