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On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH
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...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7554727/ https://www.ncbi.nlm.nih.gov/pubmed/32957651 http://dx.doi.org/10.3390/ijms21186831 |
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author | Pizzolitto, Chiara Cok, Michela Asaro, Fioretta Scognamiglio, Francesca Marsich, Eleonora Lopez, Francesco Donati, Ivan Sacco, Pasquale |
author_facet | Pizzolitto, Chiara Cok, Michela Asaro, Fioretta Scognamiglio, Francesca Marsich, Eleonora Lopez, Francesco Donati, Ivan Sacco, Pasquale |
author_sort | Pizzolitto, Chiara |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7554727 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-75547272020-10-14 On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH Pizzolitto, Chiara Cok, Michela Asaro, Fioretta Scognamiglio, Francesca Marsich, Eleonora Lopez, Francesco Donati, Ivan Sacco, Pasquale Int J Mol Sci Article 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. MDPI 2020-09-17 /pmc/articles/PMC7554727/ /pubmed/32957651 http://dx.doi.org/10.3390/ijms21186831 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Pizzolitto, Chiara Cok, Michela Asaro, Fioretta Scognamiglio, Francesca Marsich, Eleonora Lopez, Francesco Donati, Ivan Sacco, Pasquale On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH |
title | On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH |
title_full | On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH |
title_fullStr | On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH |
title_full_unstemmed | On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH |
title_short | On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH |
title_sort | on the mechanism of genipin binding to primary amines in lactose-modified chitosan at neutral ph |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7554727/ https://www.ncbi.nlm.nih.gov/pubmed/32957651 http://dx.doi.org/10.3390/ijms21186831 |
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