Synthesis of 1-deoxy-D-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate

Authors
Glomb, MA Pfahler, C
Citation
Ma. Glomb et C. Pfahler, Synthesis of 1-deoxy-D-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate, CARBOHY RES, 329(3), 2000, pp. 515-523
Citations number
16
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
329
Issue
3
Year of publication
2000
Pages
515 - 523
Database
ISI
SICI code
0008-6215(20001117)329:3<515:SO1AMH>2.0.ZU;2-W
Abstract
1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of e thoxyvinyllithium with an erythrono-lactone derivative. Characterization by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed the C-2(5)-chair beta -pyranose as the major isomer in solution. Experiments as sessing browning and polymerization reactivity proved I-DG to be a much mor e potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose. (C) 2000 El sevier Science Ltd. All rights reserved.