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.
|Digital Object Identifier (DOI):||http://dx.doi.org/10.3390/ijms21186831|
|Codice identificativo ISI:||WOS:000580318100001|
|Codice identificativo Scopus:||2-s2.0-85091167414|
|Titolo:||On the mechanism of genipin binding to primary amines in lactose-modified chitosan at neutral pH|
|Appare nelle tipologie:||1.1 Articolo in rivista|