Determination of the absolute configuration of (-)-(3R)-O-β-D- glucopyranosyloxy-5-phenylpentanoic acid from polygonum salicifolium

Chirality

Volumn 12, Issue 3, 2000, Pages 139-142

  Ganci, Walter M ^a   Kuruüzüm, Ayşe ^b   Çaliş, Ihsan ^b   Rüedi, Peter ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b HACETTEPE UNIVERSITY   (Turkey)

Author keywords

Absolute configuration; Baker's yeast reduction; Chiral HPLC; Enantioselective hydrogenation; Methyl (+) (R) and ( ) (S) 3 hydroxy 5 phenylpentanoates

Indexed keywords

3 HYDROXY 5 PHENYLPENTANOIC ACID; BETA GLUCOSIDASE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG ISOLATION; DRUG STRUCTURE; ENANTIOMER; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; NONHUMAN; PLANT; PRIORITY JOURNAL;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSIDES; POLYGONACEAE; STEREOISOMERISM;

EID: 0343986402     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(2000)12:3<139::AID-CHIR6>3.0.CO;2-3     Document Type: Article

References (13)

1. Çaliş İ, Kuruüzüm A, Demirezer LÖ, Sticher O, Ganci W, Rüedi P. Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium. J Nat Prod 1999;62:1101-1105.
2. Spino C, Mayes N, Desfossés H, Sotheeswaran S. Enantioselective synthesis of (+)- and (-)-dihydrokawanin. Tetrahedron Lett 1996;37: 6503-6506.
3. Harada T, Yoshida T, Kagamihara Y, Oku A. Resolution and asymmetric synthesis of 3-hydroxycarboxylic acids by using (-)-menthone as a chiral template. J Chem Soc Chem Commun 1993:1367-1368.
4. Fujisawa T, Fujimura A, Sato T. A general method for the synthesis of both enantiomers of optically pure β-hydroxy esters from (S)-(p-chlorophenylsulfinyl)acetone easily obtainable by kinetic resolution with bakers'yeast. Bull Chem Soc Jpn 1988;61:1273-1279.
5. Huckin SN, Weiler L. Alkylation of dianions of β-keto esters. J Am Chem Soc 1974;96:1082-1087.
6. a) Noyori R, Ohkuma T, Kitamura M, Takaya H, Sayo N, Kumobayashi H, Akutagawa S. Asymmetric hydrogenation of β-keto carboxylic esters. A practical, purely chemical access to β-hydroxy esters in high enantiomeric purity. J Am Chem Soc 1987;109:5856-5858.
7. b) Kitamura M, Ohkuma T, Inoue S, Sayo N, Kumobayashi H, Akutagawa S, Ohta T, Takaya H, Noyori R. Homogeneous asymmetric hydrogenation of functionalized ketones. J Am Chem Soc 1988;110:629-631.
8. a) Csuk R, Glänzer BI. Baker's yeast mediated transformations in organic chemistry. Chem Rev 1991;91:49-97.
9. b) Wong C-H, Whitesides GM. Enzymes in synthetic organic chemistry. Oxford: Pergamon; 1995. p 139-141.
10. Theil F. Enzyme in der Organischen Synthese. Heidelberg: Spektrum Akademischer Verlag; 1998. p 115-164.
11. a) Glänzer BI, Faber K, Griengel H, Röhr M, Wöhrer W. Enantioselective hydrolysis of esters of secondary alcohols using lyophilized bakers' yeast. Enzyme Microb Technol 1988;10:744-749.
12. b) Capozzi G, Roelens S, Talami S. A protocol for the efficient synthesis of enantiopure β-substituted β-lactones. J Org Chem 1993;58:7932-7936.
13. Fujita T, Terato K, Nakayama M. Two jasmonoid glucosides and a phenylvaleric acid glucoside from Perilla frutescens. Biosci Biotech Biochem 1996;60:723-735.