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Article

On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH

1
Department of Medical, Surgical, and Health Sciences, University of Trieste, piazza dell’Ospitale 1, 34127 Trieste, Italy
2
Department of Life Sciences, University of Trieste, via Licio Giorgieri 5, 34127 Trieste, Italy
3
Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Licio Giorgieri 1, 34127 Trieste, Italy
4
Department of Agricultural, Environmental and Food Sciences (DiAAA), University of Molise, Via De Sanctis, I-86100 Campobasso, Italy
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(18), 6831; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21186831
Received: 12 August 2020 / Revised: 14 September 2020 / Accepted: 15 September 2020 / Published: 17 September 2020
The present manuscript deals with the elucidation of the mechanism of genipin binding by primary amines at neutral pH. UV-VIS and CD measurements both in the presence of oxygen and in oxygen-depleted conditions, combined with computational analyses, led to propose a novel mechanism for the formation of genipin derivatives. The indications collected with chiral and achiral primary amines allowed interpreting the genipin binding to a lactose-modified chitosan (CTL or Chitlac), which is soluble at all pH values. Two types of reaction and their kinetics were found in the presence of oxygen: (i) an interchain reticulation, which involves two genipin molecules and two polysaccharide chains, and (ii) a binding of one genipin molecule to the polymer chain without chain–chain reticulation. The latter evolves in additional interchain cross-links, leading to the formation of the well-known blue iridoid-derivatives. View Full-Text
Keywords: primary amines; genipin as ligand; lactose-modified chitosan; neutral pH; mechanism of reaction primary amines; genipin as ligand; lactose-modified chitosan; neutral pH; mechanism of reaction
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MDPI and ACS Style

Pizzolitto, C.; Cok, M.; Asaro, F.; Scognamiglio, F.; Marsich, E.; Lopez, F.; Donati, I.; Sacco, P. On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH. Int. J. Mol. Sci. 2020, 21, 6831. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21186831

AMA Style

Pizzolitto C, Cok M, Asaro F, Scognamiglio F, Marsich E, Lopez F, Donati I, Sacco P. On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH. International Journal of Molecular Sciences. 2020; 21(18):6831. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21186831

Chicago/Turabian Style

Pizzolitto, Chiara, Michela Cok, Fioretta Asaro, Francesca Scognamiglio, Eleonora Marsich, Francesco Lopez, Ivan Donati, and Pasquale Sacco. 2020. "On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH" International Journal of Molecular Sciences 21, no. 18: 6831. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21186831

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