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Heterochirality Restricts the Self-Assembly of Phenylalanine Dipeptides Capped with Highly Aromatic Groups

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Issue date
2020
Author
Gil, Ana M.
Casanovas Salas, Jordi
Mayans, Enric
Jiménez, Ana I.
Puiggalí, Jordi
Alemán, Carlos
Suggested citation
Gil, Ana M.; Casanovas Salas, Jordi; Mayans, Enric; Jiménez, Ana I.; Puiggalí, Jordi; Alemán, Carlos; . (2020) . Heterochirality Restricts the Self-Assembly of Phenylalanine Dipeptides Capped with Highly Aromatic Groups. Journal of Physical Chemistry B, 2020, vol. 124, núm. 28, p. 5913-5918. https://doi.org/10.1021/acs.jpcb.0c04513.
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Abstract
The influence of stereochemistry on the self-assembly of phenylalanine (Phe) dipeptides bearing aromatic fluorenyl groups at both the N- and C-termini (Fmoc, OFm) has been investigated. For this purpose, Fmoc–d-Phe–l-Phe–OFm and Fmoc–l-Phe–l-Phe–OFm have been examined considering a wide variety of solvents, which differ in dielectric constant and volatility. Results reveal that replacement of l-Phe by d-Phe has a major impact on the self-assembly propensities, restricting drastically the structural diversity and polymorphism shown by the homochiral dipeptide. Thus, the analogous heterochiral dipeptide shows a great propensity to form micro/nanofibers, independently of the environmental conditions. Theoretical calculations revealed that the stability of antiparallel disposition is much higher (a factor of ca. 15) for Fmoc–d-Phe–l-Phe–OFm than that for Fmoc–l-Phe–l-Phe–OFm, which has been attributed to the hydrophobic core formed in the former. Overall, results suggest that control of the backbone chirality is a potent and versatile strategy to drive and finely tune the self-assembly propensities of highly aromatic peptides.
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http://hdl.handle.net/10459.1/73027
DOI
https://doi.org/10.1021/acs.jpcb.0c04513
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Journal of Physical Chemistry B, 2020, vol. 124, núm. 28, p. 5913-5918
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