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Polymorphism of L-tryptophan

Al Rahal, Okba, Hughes, Colan E., Williams, P. Andrew, Logsdail, Andrew J. ORCID:, Diskin-Posner, Yael and Harris, Kenneth D. M. ORCID: 2019. Polymorphism of L-tryptophan. Angewandte Chemie International Edition 58 (52) , pp. 18788-18792. 10.1002/anie.201908247

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A new polymorph of L‐tryptophan has been prepared by crystallization from the gas phase, with structure determination carried out directly from powder XRD data augmented by periodic DFT‐D calculations. The new polymorph (denoted β) and the previously reported polymorph (denoted α) are both based on alternating hydrophilic and hydrophobic layers, but with substantially different hydrogen‐bonding arrangements. The β polymorph exhibits the energetically favourable L2‐L2 hydrogen‐bonding arrangement, which is unprecedented for amino acids with aromatic side‐chains; the specific molecular conformations adopted in the β polymorph facilitate this hydrogen‐bonding scheme while avoiding steric conflict of the side‐chains.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 1433-7851
Date of First Compliant Deposit: 24 October 2019
Date of Acceptance: 11 October 2019
Last Modified: 06 Nov 2023 18:10

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