Format

Send to

Choose Destination
Biosci Biotechnol Biochem. 2017 Feb;81(2):343-349. doi: 10.1080/09168451.2016.1240607. Epub 2016 Oct 6.

Two novel pyrrolooxazole pigments formed by the Maillard reaction between glucose and threonine or serine.

Author information

1
a Department of Nutrition and Food Science , Ochanomizu University , Tokyo , Japan.

Abstract

Pyrrolothiazolate formed by the Maillard reaction between l-cysteine and d-glucose has a pyrrolothiazole skeleton as a chromophore. We searched for a Maillard pigment having a pyrrolooxazole skeleton formed from l-threonine or l-serine instead of l-cysteine in the presence of d-glucose. As a result, two novel yellow pigments, named pyrrolooxazolates A and B, were isolated from model solutions of the Maillard reaction containing l-threonine and d-glucose, and l-serine and d-glucose, respectively, and identified as (2R,3S,7aS)-2,3,7,7a-tetrahydro-6-hydroxy-2,5,7a-trimethyl-7-oxo-pyrrolo[2,1-b]oxazole-3-calboxylic acid and (3S,7aS)-2,3,7,7a-tetrahydro-6-hydroxy-5,7a-dimethyl-7-oxo-pyrrolo[2,1-b]oxazole-3-calboxylic acid by instrumental analyses. These compounds were pyrrolooxazole derivatives carrying a carboxy group, and showed the absorption maxima at 300-360 nm under acidic and neutral conditions and at 320-390 nm under alkaline conditions.

KEYWORDS:

Maillard reaction; browning; pyrrolooxazole; threonine; yellow

PMID:
27710213
DOI:
10.1080/09168451.2016.1240607
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Taylor & Francis
Loading ...
Support Center