Synthesis of 4-deoxyquinic, 4-deoxyshikimic and 4-deoxy-3-dehydroshikimic acids

Authors
Gonzalez-Bello, C Coggins, JR Hawkins, AR Abell, C
Citation
C. Gonzalez-bello et al., Synthesis of 4-deoxyquinic, 4-deoxyshikimic and 4-deoxy-3-dehydroshikimic acids, J CHEM S P1, (8), 1999, pp. 849-854
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
8
Year of publication
1999
Pages
849 - 854
Database
ISI
SICI code
0300-922X(19990421):8<849:SO44A4>2.0.ZU;2-S
Abstract
The synthesis of 4-deoxyquinic acid (1b) from (-)-quinic acid (1a) and 4-de oxyshikimic acid (4b) from shikimic acid (4a) respectively are described. 4 -Deoxyshikimic acid (4b) was converted enzymatically into 4-deoxy-3-dehydro shikimic acid (3b) using shikimate dehydrogenase. The C(4) hydroxy group is shown not to contribute significantly to substrate specificity for shikima te dehydrogenase. Attempts to synthesise 4-deoxy-3-dehydroquinic acid (2b) are described.