Synthesis and Stereochemistry of (E)-5-(3,4,5,6-Tetrahydropyrid-3-ylidenemethyl)-2-furanmethanol, a Product of the Reaction between D-Glucose and L-Lysine.

Miller, Raya; Edlund, Ulf; Ubeda, Danielle C. N.; Müller, Franz; Sjöstróm, Michael

doi:10.3891/acta.chem.scand.41b-0208

Cited by 11 publications

(13 citation statements)

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“…1). Miller (1987) synthesized this compound from furfural and 2, 3, 4, 5-tetrahydropyridine. There is no report that 2 is formed from a solution containing furfural or pentose, and lysine.…”

Section: Resultsmentioning

confidence: 99%

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A Novel Yellow Compound and Furpipate Derivatives Formed from Furfural or 5-Hydroxymethylfurfural in the Presence of Lysine

Totsuka

Tokuzen

Ono

et al. 2009

FSTR

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Section: Resultsmentioning

confidence: 99%

“…1). This compound was found as a product of the reaction between glucose and lysine in slightly acidic aqueous solution (Miller et al, 1984) and was synthesized from 5-hydroxymethylfurfural and 2, 3, 4, 5-tetrahydropyridine (Miller, 1987).…”

Section: Isolation and Identification Of 5-hydroxymethylfurpipate (3)mentioning

confidence: 99%

A Novel Yellow Compound and Furpipate Derivatives Formed from Furfural or 5-Hydroxymethylfurfural in the Presence of Lysine

Totsuka

Tokuzen

Ono

et al. 2009

FSTR

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“…HMF and 1,2-dehydropiperidine undergo aldo condensation and dehydration to form F3-A. 21 Chemical Properties and Chemical Structure of [5-(5,6-Dihydro-4H-pyridin-3-ylidenemethyl)-furan-2-yl]-methanol. The HPLC profile of Glc-Lys heated mixture is shown in Figure 1 Small amounts of F3-AC19 were dissolved in CD 3 OD; 1 H, 13 C, COSY, 13 C-APT, HSQC, and HMBC-NMR experiments were performed.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Elucidation of the Chemical Structure and Determination of the Production Conditions for a Bioactive Maillard Reaction Product, [5-(5,6-Dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl]methanol, Isolated from a Glucose–Lysine Heated Mixture

Chen

et al. 2015

J. Agric. Food Chem.

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We previously isolated a bioactive molecule, named F3-A, from an aqueous glucose (Glc) and lysine (Lys) Maillard reaction (MR) model system. Herein, F3-A was verified as [5-(5,6-dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl]methanol (5) and was subsequently synthesized for confirmation of bioactivity. Using Taguchi and factorial designs, we determined that the conditions which best increased the yield of F3-A were at pH 6 with a sugar:amino acid ratio of 2:1 and heating time of 12 h at 100 °C. The MR mixtures containing glucose produced highest yield, compared to fructose, lactose, and sucrose. Both the F3-A recovered from Glc-Lys MR mixture and the synthesized product exhibited significant (P < 0.05), dose dependent, nitric oxide (NO) inhibitory activity in Caco-2 cells that was comparable to aminoguanidine (AG) and pyrrolidine dithiocarbamate (PDTC), respectively. Finally, an additional inhibitory effect of F3-A was determined when coincubated with AG in cytokine-induced Caco-2 cells. This bioactivity points to a potential role in preventing intestinal inflammation.

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“…We then isolated this compound and identified it by instrumental analyses, such as MS and NMR, as decarboxylated‐furpipate ( 1 [7]). This compound had been synthesized from furfural and 2,3,4,5‐tetrahydropyridine 10 …”

Section: Resultsmentioning

confidence: 99%

“… Chemical structures of the colored compounds derived from furfural ( 1 , 3 2a and 2b , 3,4 6 , 8 and 7 10 ) and pentose ( 3 , 5 4 , 6 and 5 7 ) with amino acids. …”

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confidence: 99%

A Novel Yellow Pigment, Furpipate, Derived from Lysine and Furfural

Murata

Totsuka

Ono

2008

Annals of the New York Academy of Sciences

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Furfural is an important intermediate compound of the Maillard reaction of pentose or ascorbic acid. We examined the browning of furfural and lysine by heating these compounds in solution and found two yellow compounds. The first, furpipate, is a novel pipecolic acid derivative and was (Z)-3-(2-furylmethylidene)-3H, 4H, 5H, 6H-pyridine-2-carboxylic acid. The second was decarboxylated-furpipate. Furpipate shows absorption maxima at 370 nm and 310 nm under acidic and alkaline conditions, respectively. This compound was the major colored compound of the heated solution containing lysine and furfural.

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Synthesis and Stereochemistry of (E)-5-(3,4,5,6-Tetrahydropyrid-3-ylidenemethyl)-2-furanmethanol, a Product of the Reaction between D-Glucose and L-Lysine.

Cited by 11 publications

References 0 publications

A Novel Yellow Compound and Furpipate Derivatives Formed from Furfural or 5-Hydroxymethylfurfural in the Presence of Lysine

A Novel Yellow Compound and Furpipate Derivatives Formed from Furfural or 5-Hydroxymethylfurfural in the Presence of Lysine

Elucidation of the Chemical Structure and Determination of the Production Conditions for a Bioactive Maillard Reaction Product, [5-(5,6-Dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl]methanol, Isolated from a Glucose–Lysine Heated Mixture

A Novel Yellow Pigment, Furpipate, Derived from Lysine and Furfural

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