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

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dc.contributor.author Hayes, John A.
dc.contributor.author Eccles, Kevin S.
dc.contributor.author Lawrence, Simon E.
dc.contributor.author Moynihan, Humphrey A.
dc.date.accessioned 2016-07-25T10:27:09Z
dc.date.available 2016-07-25T10:27:09Z
dc.date.issued 2016-03-14
dc.identifier.citation Hayes, 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.2016.01.012 en
dc.identifier.volume 425 en
dc.identifier.startpage 35 en
dc.identifier.endpage 39 en
dc.identifier.issn 0008-6215
dc.identifier.uri http://hdl.handle.net/10468/2934
dc.identifier.doi 10.1016/j.carres.2016.01.012
dc.description.abstract Methyl 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.sponsorship Science 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.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Elsevier Ltd en
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.uri https://creativecommons.org/licenses/by-nc-nd/4.0/ en
dc.subject Methyl tetra-O-acetyl-d-glucopyranuronate en
dc.subject Crystallisation of anomers en
dc.title Methyl tetra-O-acetyl-α-d-glucopyranuronate: crystal structure and influence on the crystallisation of the β anomer en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Humphrey Moynihan, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: h.moynihan@ucc.ie en
dc.internal.availability Full text not available en
dc.check.info Access to this article is restricted until 24 months after publication by the request of the publisher. en
dc.check.date 2018-03-14
dc.date.updated 2016-07-22T15:33:48Z
dc.description.version Accepted Version en
dc.internal.rssid 357192299
dc.contributor.funder Irish Research Council for Science Engineering and Technology en
dc.contributor.funder Science Foundation Ireland en
dc.contributor.funder University College Cork
dc.description.status Peer reviewed en
dc.identifier.journaltitle Carbohydrate Research en
dc.internal.copyrightchecked Yes en
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress h.moynihan@ucc.ie en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en


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© 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/ Except where otherwise noted, this item's license is described as © 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/
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