143615-30-9Relevant academic research and scientific papers
Regioselective enzymatic acylation of methyl shikimate. Influence of acyl chain length and solvent polarity on enzyme specificity.
Armesto, Nuria,Ferrero, Miguel,Fernandez, Susana,Gotor, Vicente
, p. 4978 - 4981 (2002)
Candida antarctica lipase A (CAL-A) selectively catalyzes the acylation at the secondary C-4 hydroxyl group of methyl shikimate (2), which possesses three secondary hydroxyl groups, the C-3 allylic one being chemically more reactive. The effect both of the acyl group of the acylating agents and of the solvent polarity has been studied. The selectivity of CAL-A is almost complete with acyl donors that possess short chains. However, when acyl donors have longer chains, better results are obtained by C. antarctica lipase B (CAL-B).
Influence of intramolecular hydrogen bonds in the enzyme-catalyzed regioselective acylation of quinic and shikimic acid derivatives
Armesto, Nuria,Fernández, Susana,Ferrero, Miguel,Gotor, Vicente
, p. 5401 - 5410 (2007/10/03)
Selective mono-functionalization of 3-epi, 4-epi-, and 5-epi quinic and shikimic acid derivatives has been accomplished by enzymatic acylation with Candida antarctica lipase A (CAL-A). We propose that the selectivity of this lipase is related to both the
Novel enzymatic synthesis of 4-O-cinnamoyl quinic and shikimic acid derivatives
Armesto, Nuria,Ferrero, Miguel,Fernandez, Susana,Gotor, Vicente
, p. 5784 - 5787 (2007/10/03)
The first direct synthesis of 4-O-cinnamoyl derivatives of quinic and shikimic acids were accomplished by regioselective esterification with Candida antarctica lipase A. For hydrocinnamic esters, enzymatic transesterification with vinyl esters gave excell
Studies on the Enzymatic Acylation of Quinic Acid, Shikimic Acid, and Their Derivatives in Organic Solvents
Danieli, Bruno,Bellis, Paolo De,Barzaghi, Laura,Carrea, Giacomo,Ottolina, Gianluca,Riva, Sergio
, p. 1297 - 1304 (2007/10/02)
Quinic acid (1a), shikimic acid (2), and their derivatives were acylated in organic solvents by several lipases and by the protease subtilisin Carlsberg.The most satisfactory results were obtained with methyl(or benzyl) quinate (7a (or8a)) and lipase from
AN IMPROVED SYNTHESIS OF (+/-)-METHYL SHIKIMATE THROUGH STEREOSELECTIVE CIS-DIHYDROXYLATION OF (+/-)-METHYL 5β-HYDROXYCYCLOHEXA-1,3-DIENOATE UNDER PREVOST'S REACTION CONDITIONS
Campbell, Malcolm M.,Sainsbury, Malcolm,Yavarzadeh, Roya
, p. 5063 - 5070 (2007/10/02)
A Prevost-type reaction under "wet" conditions upon the O-t-butyl-dimethylsilyl derivative of (+/-)-methyl 5β-hydroxycyclohexa-1,3-dienoate gives (+/-)-methyl 3α-acetoxy-4β-hydroxy-5β-t-butyldimethylsilyloxycyclohexene which may be readily deprotected to afford (+/-)-methyl shikimate in very high yield.Less selectivity is observed in a similar reaction upon the parent alcohol and when this compound is reacted under dry conditions the major product is (+/-)-methyl 4β,5β-epoxy-3β-acetoxycyclohexenoate.An analysis of Prevost reactions with exo and endo methyl 7-oxabicyclohept-5-en-2-oate is also described.
