On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH.
Amines
/ chemistry
Biocompatible Materials
/ chemistry
Chitosan
/ analogs & derivatives
Circular Dichroism
Computational Chemistry
Cross-Linking Reagents
/ chemistry
Hydrogen-Ion Concentration
Iridoids
/ chemistry
Kinetics
Lactose
/ chemistry
Ligands
Magnetic Resonance Spectroscopy
Oxygen
/ chemistry
Polysaccharides
/ chemistry
Spectrophotometry, Ultraviolet
genipin as ligand
lactose-modified chitosan
mechanism of reaction
neutral pH
primary amines
Journal
International journal of molecular sciences
ISSN: 1422-0067
Titre abrégé: Int J Mol Sci
Pays: Switzerland
ID NLM: 101092791
Informations de publication
Date de publication:
17 Sep 2020
17 Sep 2020
Historique:
received:
12
08
2020
revised:
14
09
2020
accepted:
15
09
2020
entrez:
22
9
2020
pubmed:
23
9
2020
medline:
16
3
2021
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 32957651
pii: ijms21186831
doi: 10.3390/ijms21186831
pmc: PMC7554727
pii:
doi:
Substances chimiques
Amines
0
Biocompatible Materials
0
Cross-Linking Reagents
0
Iridoids
0
Ligands
0
Polysaccharides
0
Chitosan
9012-76-4
genipin
A3V2NE52YG
Lactose
J2B2A4N98G
Oxygen
S88TT14065
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Interreg
ID : 1472551605
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