Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine.

Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine. Research Abstract Details 

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Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine. Abstract Text:

Zhenyu Dai,Ina Nemet,Wei Shen,Vincent M Monnier,

We isolated a novel acid-labile yellow chromophore from the incubation of lysine, histidine and d-threose and identified its chemical structure by one and two-dimensional NMR spectroscopy combined with LC-tandem mass spectrometry. This new cross-link exhibits a UV absorbance maximum at 305 nm and a molecular mass of 451 Da. The proposed structure is 2-amino-5-(3-((4-(2-amino-2-carboxyethyl)-1H-imidazol-1-yl)methyl)-4-(1,2-dihydroxyethyl)-2-formyl-1H-pyrrol-1-yl)pentatonic acid, a cross-link between lysine and histidine with addition of two threose molecules. It was in part deduced and confirmed through synthesis of the analogous compound from n-butylamine, imidazole and d-threose. We assigned the compound the trivial name histidino-threosidine. Systemic incubation revealed that histidino-threosidine can be formed in low amounts from fructose, glyceraldehyde, methylglyoxal, glycolaldehyde, ascorbic acid, and dehydroascorbic acid, but at a much higher yield with degradation products of ascorbic acid, i.e. threose, erythrose, and erythrulose. Bovine lens protein incubated with 10 and 50 mM threose for two weeks yielded 560 and 2840 pmol/mg histidino-threosidine. Histidino-threosidine is to our knowledge the first Maillard reaction product known to involve histidine in a crosslink.

Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine. Publishing Authors By Initials

Z Dai,I Nemet,W Shen,VM Monnier,

For similar carbohydrates: monosaccharides: tetroses research abstracts see: carbohydrates: monosaccharides: tetroses research

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Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Archives of biochemistry and biophysics

VOLUME: 463

Page Numbers: 78-88

Journal Abbreviation: Arch. Biochem. Biophys.

ISSN: 0003-9861

DAY: 2

MONTH: 04

YEAR: 2007

Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine. Information

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LANGUAGE: eng

NlmUniqueID: 372430

Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine. Keywords Mesh Terms:

KEYWORDS: Tetroses

MESH TERMS: metabolism

Chemical & Substance for Abstract: Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine. Information

Substance Name: Histidine

Registry Number: 71-00-1

Grant and Affiliation Information for Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine.

AFFILIATION: Department of Biochemistry, Case Western Reserve University, Cleveland, OH 44106, USA.

Country: United States

AGENCY: United States NEI

GRANT: EY07099

ACRONYM: EY

MEDLINETA: Arch Biochem Biophys

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