Alpha 2.0
Login Register
» Articles » PMID: 21456563

Molecular Structure of Humin and Melanoidin Via Solid State NMR

Overview
Journal J Phys Chem B
Publisher American Chemical Society
Specialty Chemistry
Date 2011 Apr 5
PMID 21456563
Citations 4
Authors
Judith Herzfeld
Danielle Rand
Yoh Matsuki
Eugenio Daviso
Melody Mak-Jurkauskas
Irena Mamajanov
Affiliations
Soon will be listed here.
Abstract

Sugar-derived humins and melanoidins figure significantly in food chemistry, agricultural chemistry, biochemistry, and prebiotic chemistry. Despite wide interest and significant experimental attention, the amorphous and insoluble nature of the polymers has made them resistant to conventional structural characterization. Here we make use of solid-state NMR methods, including selective (13)C substitution, (1)H-dephasing, and double quantum filtration. The spectra, and their interpretation, are simplified by relying exclusively on hydronium for catalysis. The results for polymers derived from ribose, deoxyribose, and fructose indicate diverse pathways to furans, suggest a simple route to pyrroles in the presence of amines, and reveal a heterogeneous network-type polymer in which sugar molecules cross-link the heterocycles.

Citing Articles

Characterization of volatile compounds and sensory properties of spine grape ( Foex) brandies aged with different toasted wood chips.

Duan B, Chang W, Zhang L, Zheng M, Su-Zhou C, Merkeryan H Food Chem X. 2024; 23:101777.

PMID: 39295964 PMC: 11408013. DOI: 10.1016/j.fochx.2024.101777.

Synthesis of Resins Using Epoxies and Humins as Building Blocks: A Mechanistic Study Based on In-Situ FT-IR and NMR Spectroscopies.

Montane X, Dinu R, Mija A Molecules. 2019; 24(22).

PMID: 31739442 PMC: 6891716. DOI: 10.3390/molecules24224110.

Condensation of α-Carbonyl Aldehydes Leads to the Formation of Solid Humins during the Hydrothermal Degradation of Carbohydrates.

Shi N, Liu Q, Ju R, He X, Zhang Y, Tang S ACS Omega. 2019; 4(4):7330-7343.

PMID: 31459833 PMC: 6648842. DOI: 10.1021/acsomega.9b00508.

Synthesis of Humin-Phenol-Formaldehyde Adhesive.

Kang S, Fu J, Zhang G, Zhang W, Yin H, Xu Y Polymers (Basel). 2019; 9(8).

PMID: 30971051 PMC: 6418814. DOI: 10.3390/polym9080373.

References
1.
Antal Jr M, Mok W, Richards G . Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose an sucrose. Carbohydr Res. 1990; 199(1):91-109. DOI: 10.1016/0008-6215(90)84096-d. View
2.
Tressl , Wondrak , KRUGER , Rewicki . New Melanoidin-like Maillard Polymers from 2-Deoxypentoses. J Agric Food Chem. 2001; 46(1):104-110. DOI: 10.1021/jf970657c. View
3.
Nimlos M, Qian X, Davis M, Himmel M, Johnson D . Energetics of xylose decomposition as determined using quantum mechanics modeling. J Phys Chem A. 2006; 110(42):11824-38. DOI: 10.1021/jp0626770. View
4.
Rand D, Belenky M, Herzfeld J . Microspherules from sugars in the absence of nitrogen. Orig Life Evol Biosph. 2010; 41(1):17-22. DOI: 10.1007/s11084-010-9218-x. View
5.
Yaylayan V . Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions, and spectroscopic properties. Crit Rev Food Sci Nutr. 1994; 34(4):321-69. DOI: 10.1080/10408399409527667. View