Gas-Phase Enantioselectivity of Chiral N-Linked Peptidoresorc[4]arene Isomers toward Dipeptides

Botta B, Fraschetti C, D'Acquarica I, Speranza M, Novara FR, Mattay J, Letzel M (2009)
Journal of Physical Chemistry A 113(52): 14625-14629.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
The gas-phase enantioselectivity of cone N-linked peptidoresorc[4]arenes (generally symbolized as M) toward the homologue dipeptides (generally symbolized as A) has been evaluated by measuring the kinetics of the A release from the diastereomeric [M center dot H center dot A](+) complexes induced by (R)-(-)-2-butylamine (B). In most cases investigated, the heterochiral [M center dot H center dot A](+) complexes, namely those wherein the configuration of the A guest is opposite to that or the host M pendants, react faster (up to 5 times) than the homochiral analogues, wherein guest A guest has the same Configuration of the host M pendants. The kinetic results, discussed in the light of previous MS and NMR evidence, indicate that both the efficiency and the enantioselectivity of the guest exchange reaction depend essentially on the Structure and the relative stability of the diastereomeric [M center dot H center dot A](+) complexes. These, in turn, depend oil the functional groups and the configuration of both the guest and the host pendants. The absence of any significant effects of the B configuration indicates that, in all systems investigated, the dipeptide guest A is predominantly located outside the host chiral cavity.
Erscheinungsjahr
Zeitschriftentitel
Journal of Physical Chemistry A
Band
113
Zeitschriftennummer
52
Seite
14625-14629
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Botta B, Fraschetti C, D'Acquarica I, et al. Gas-Phase Enantioselectivity of Chiral N-Linked Peptidoresorc[4]arene Isomers toward Dipeptides. Journal of Physical Chemistry A. 2009;113(52):14625-14629.
Botta, B., Fraschetti, C., D'Acquarica, I., Speranza, M., Novara, F. R., Mattay, J., & Letzel, M. (2009). Gas-Phase Enantioselectivity of Chiral N-Linked Peptidoresorc[4]arene Isomers toward Dipeptides. Journal of Physical Chemistry A, 113(52), 14625-14629. doi:10.1021/jp904374h
Botta, B., Fraschetti, C., D'Acquarica, I., Speranza, M., Novara, F. R., Mattay, J., and Letzel, M. (2009). Gas-Phase Enantioselectivity of Chiral N-Linked Peptidoresorc[4]arene Isomers toward Dipeptides. Journal of Physical Chemistry A 113, 14625-14629.
Botta, B., et al., 2009. Gas-Phase Enantioselectivity of Chiral N-Linked Peptidoresorc[4]arene Isomers toward Dipeptides. Journal of Physical Chemistry A, 113(52), p 14625-14629.
B. Botta, et al., “Gas-Phase Enantioselectivity of Chiral N-Linked Peptidoresorc[4]arene Isomers toward Dipeptides”, Journal of Physical Chemistry A, vol. 113, 2009, pp. 14625-14629.
Botta, B., Fraschetti, C., D'Acquarica, I., Speranza, M., Novara, F.R., Mattay, J., Letzel, M.: Gas-Phase Enantioselectivity of Chiral N-Linked Peptidoresorc[4]arene Isomers toward Dipeptides. Journal of Physical Chemistry A. 113, 14625-14629 (2009).
Botta, Bruno, Fraschetti, Caterina, D'Acquarica, Ilaria, Speranza, Maurizio, Novara, Francesca R., Mattay, Jochen, and Letzel, Matthias. “Gas-Phase Enantioselectivity of Chiral N-Linked Peptidoresorc[4]arene Isomers toward Dipeptides”. Journal of Physical Chemistry A 113.52 (2009): 14625-14629.

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Kinetic enantioselectivity of a protonated bis(diamido)-bridged basket resorcin[4]arene towards alanine peptides.
Fraschetti C, Montagna M, Crestoni ME, Calcaterra A, Aiello F, Santi L, Filippi A., Org Biomol Chem 15(5), 2017
PMID: 28084488
Hydrolytic inhibition of α-chymotrypsin by 2,8,14,20-tetrakis(D-leucyl-D-valinamido)resorc[4]arenecarboxylic acid: a spectroscopic NMR and computational combined approach.
Uccello-Barretta G, Balzano F, Aiello F, Vanni L, Mori M, Menta S, Calcaterra A, Botta B., Org Biomol Chem 13(3), 2015
PMID: 25406985
Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase.
Fraschetti C, Letzel MC, Paletta M, Mattay J, Speranza M, Filippi A, Aschi M, Rozhenko AB., J Mass Spectrom 47(1), 2012
PMID: 22282092

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