2005
DOI: 10.1002/bit.20721
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Synthesis of enantiomerically pure trans‐(1R,2R)‐ and cis‐(1S,2R)‐1‐amino‐2‐indanol by lipase and ω‐transaminase

Abstract: Syntheses of trans-(1R,2R) and cis-(1S,2R)-1-amino-2-indanol (AI) were accomplished by a series of enantioselective enzymatic reactions using lipase and transaminase (TA). Lipase catalysed enantioselective hydrolysis of 2-acetoxyindanone was employed to prepare (R)-2-hydroxy indanone (HI). trans-AI (5 mM) (de > 98%) was produced from 20 mM (R)-2- HI using omega-TA and 50 mM (S)-1-aminoindan as an amino donor in water-saturated ethyl acetate. For the production of cis-AI, the diastereomeric (2R)-AI was synthesi… Show more

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Cited by 38 publications
(27 citation statements)
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“…3.1.1.3) is an important class of enzymes with numerous applications in the rapidly growing biotechnology and biomedical fields [1][2][3][4][5][6][7][8]. Lipase hydrolyzes the carboxyl ester bonds in mono-, di-and tri-glycerides to liberate fatty acids and alcohols in aqueous solutions.…”
Section: Introductionmentioning
confidence: 99%
“…3.1.1.3) is an important class of enzymes with numerous applications in the rapidly growing biotechnology and biomedical fields [1][2][3][4][5][6][7][8]. Lipase hydrolyzes the carboxyl ester bonds in mono-, di-and tri-glycerides to liberate fatty acids and alcohols in aqueous solutions.…”
Section: Introductionmentioning
confidence: 99%
“…3) There are many biotechnological applications of !-TA, and successful examples in which enantiomerically pure (R)-form compounds were synthesized via !-TA-mediated kinetic resolution. [4][5][6] Asymmetric synthesis of chiral amines with !-TA (the reverse reaction of kinetic resolution) has many potential advantages over the forward reaction, including a two-fold higher theoretical yield and the ability to yield an enantiomerically pure (S)-form. Despite these properties, efficient asymmetric synthesis from ketone compounds with !-TA has not been studied as extensively as kinetic resolution.…”
mentioning
confidence: 99%
“…Recently, Yun et al [15] succeeded in synthesis of trans-(1R,2R)-1-amino-2-indanol by x-transaminase from Escherichia coli BL21, which harbored the x-TA gene from V. fluvialis JS17. A transaminase, harboring the ability to aminate the L-erythrulose to produce 2-amino-1,3,4-butanetriol, was detected from Pseudomonas aeruginosa by Ingram et al [16].…”
Section: Microbial Screeningmentioning
confidence: 99%
“…Among the transaminases, diamine-ketoglutaric transaminase, which belongs to the class of x-transaminases and the family of subclass II of aminotransferases, was the first one reported to utilize a substrate bearing no carboxylic acid group [14]. However, there are few reports showing the ability of transaminase in transformation of keto alcohols to amino alcohols, which are extremely important class of compounds of considerable pharmaceutical interest [15,16]. As transaminases are gaining increasing attention in production of high-value compounds, synthesis of amino alcohols by transaminases seem to be more promising in future.…”
Section: Introductionmentioning
confidence: 99%