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


ABSTRACT: 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.

SUBMITTER: Pizzolitto C 

PROVIDER: S-EPMC7554727 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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

Pizzolitto Chiara C   Cok Michela M   Asaro Fioretta F   Scognamiglio Francesca F   Marsich Eleonora E   Lopez Francesco F   Donati Ivan I   Sacco Pasquale P  

International journal of molecular sciences 20200917 18


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  ...[more]

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