Optimized enzymatic synthesis of caffeic acid phenethyl ester by RSM

Chen, Hsiao‐Ching; Ju, Hen-Yi; Twu, Yawo-Kuo; Chen, Jiann-Hwa; Chang, Chieh-Ming J.; Liu, Yung-Chuan; Chang, Cheng‐Nan; Shieh, Chwen‐Jen

doi:10.1016/j.nbt.2009.12.002

Cited by 29 publications

(17 citation statements)

References 12 publications

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“…In terms of the conversion yield, this procedure using Novozyme 435 is superior to the previously reported procedure affording CAPE with the maximum conversion yield of 50% (Kishimoto et al, 2005a). CAPE was obtained by transesterification catalyzed by Novozyme 435 using isooctane as the solvent with the conversion yield of 91.65% (Chen et al, 2010). The conversion yields of the CAPE analogues produced by the [bmim][NTf 2 ] system are comparable to that of CAPE produced by the isooctane system.…”

Section: Substrate Specificity For Novozyme 435mentioning

confidence: 77%

“…In the synthesis of CAPE analogues, the conversion yield of 3-cyclohexylpropyl caffeate toward 5-caffeoylquinic acid (85.3%) was superior to that of CAPE toward 5-caffeoylquinic acid (50%) (Kishimoto et al, 2005a). CAPE analogues were obtained by single transesterification systems catalyzed by Novozyme 435 using [bmim][NTf 2 ] or isooctane as the solvent with conversion yields of 93.8% and 91.65%, respectively (Chen et al, 2010;Kurata et al, 2010). The conversion yield of 3-cyclohexylpropyl caffeate produced by the consecutive conversion system was comparable to those of CAPE produced by single transesterification systems.…”

Section: Consecutive Enzymatic Reactions For Synthesis Of 3-cyclohexymentioning

confidence: 99%

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Biotransformation of Underutilized Natural Resource to Valuable Compounds in Ionic Liquid: Enzymatic Synthesis of Caffeic Acid Phenethyl Ester Analogues from Immature Coffee Beans

Kurata¹,

Fujita²,

Kishimoto³

2011

Applications of Ionic Liquids in Science and Technology

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Section: Substrate Specificity For Novozyme 435mentioning

confidence: 77%

Section: Consecutive Enzymatic Reactions For Synthesis Of 3-cyclohexymentioning

confidence: 99%

Biotransformation of Underutilized Natural Resource to Valuable Compounds in Ionic Liquid: Enzymatic Synthesis of Caffeic Acid Phenethyl Ester Analogues from Immature Coffee Beans

Kurata¹,

Fujita²,

Kishimoto³

2011

Applications of Ionic Liquids in Science and Technology

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“…As expected, ''CAPE 60'' is clearly more effective in suppressing both the growth and metastasis of MPNST in mice (16), confirming that the higher CAPE content, the more effective the propolis extract. Recently, enzymatic synthesis of CAPE was developed and further improved by a group in Taiwan (25,26). A mixture of CA and phenethyl alcohol (PA) can be converted almost 100% to CAPE by the immobilized lipase B called ''Novozym 435'' (see Figure 8).…”

Section: Wwwddtjournalcommentioning

confidence: 99%

Effective neurofibromatosis therapeutics blocking the oncogenic kinase PAK1

Miyata

2011

DD&T

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Neurofibromatosis (NF) is a family of genetic diseases which are caused by dysfunction of either NF1 gene or NF2 gene. One in 3,000 people suffer from this tumor-carrying NF. NF1 gene product is a RAS GTPase activating protein (GAP) of 2,818 amino acids, which normally attenuates the GTPdependent signal transducing activity of the G protein RAS. Dysfunction of this GAP leads to the abnormal activation of RAS, and eventually an oncogenic kinase called PAK1 as well. NF2 gene product is ''Merlin'' which directly inactivates PAK1. Thus, dysfunction of Merlin causes the abnormal activation of PAK1. In other words, dysfunction of NF1 gene (causing type 1 NF) is basically the same as dysfunction of NF2 gene (causing type 2 NF). In fact the growth of both NF1 and NF2 tumors requires PAK1, and all PAK1 blockers, synthetic chemicals or natural products, suppress the growth of these NF tumor cells both in vitro (cell culture) and in vivo (mice).However, until recently, no FDA-approved effective NF therapeutics is available on the market. Here a series of anti-PAK1 products shall be introduced, which would be potentially useful for the life-long treatment of NF patients in the future. These include the most potent HDAC (histone deacetylase) inhibitor FK228 (IC 50 : around 1 nM), that eventually blocks PAK1, the direct PAK1 inhibitor PF3758309 (IC 50 : around 10 nM), a CAPE (caffeic acid phenethyl ester)-based propolis extract called ''Bio 30'' from NZ (New Zealand), and an ARC (artepillin C)-based green propolis extract (GPE) from Brazil. Although the first two drugs are potent, none of them is available on the market as yet. The last two natural (bee-made) products are available on the market, and have been used for the therapy of NF and tuberous sclerosis (TSC) as well as many PAK1-dependent solid cancers such as breast and pancreatic cancers as well as glioma, which altogether represent more than 70% of all human cancers. Since PAK1 is not essential for the normal cell growth, propolis extracts cause no side effects.

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“…• C, substrate molar ratio 1 : 72 and 351 PLU of enzyme in an orbital shaking water bath (180 rpm); 17 ultrasound assistance. It was possible that the increasing collision effected between the two substrates and the enzyme decreased the required reaction time.…”

Section: Model Verificationmentioning

confidence: 99%

A continuous ultrasound‐assisted packed‐bed bioreactor for the lipase‐catalyzed synthesis of caffeic acid phenethyl ester

Chen

Twu

Chen

et al. 2011

J of Chemical Tech & Biotech

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BACKGROUND: The focus of this paper is the ultrasound-assisted synthesis of caffeic acid phenethyl ester (CAPE) from caffeic acid and phenyl ethanol in a continuous packed-bed bioreactor. Immobilized Novozym (R) 435 (from Candida antarctica) is used as the catalyst. A three-level-three-factor Box-Behnken design and a response surface methodology (RSM) are employed to evaluate the effects of temperature, flow rate, and ultrasonic power on the percentage molar conversion of CAPE. RESULTS: Based on ridge max analysis, it is concluded that the optimum condition for synthesis is reaction temperature 72.66 degrees C, flow rate 0.046 mL min(-1), and ultrasonic power 1.64 W cm(-2). The expected molar conversion value is 97.84%. An experiment performed under these optimal conditions resulted in a molar conversion of 92.11 +/- 0.75%. The enzyme in the bioreactor was found to be stable for at least 6 days. CONCLUSIONS: The lipase-catalyzed synthesis of CAPE by an ultrasound-assisted packed-bed bioreactor uses mild reaction conditions. Enzymatic synthesis of CAPE is suitable for use in the nutraceutical and food production industries. (C) 2011 Society of Chemical Industr

show abstract

Optimized enzymatic synthesis of caffeic acid phenethyl ester by RSM

Cited by 29 publications

References 12 publications

Biotransformation of Underutilized Natural Resource to Valuable Compounds in Ionic Liquid: Enzymatic Synthesis of Caffeic Acid Phenethyl Ester Analogues from Immature Coffee Beans

Biotransformation of Underutilized Natural Resource to Valuable Compounds in Ionic Liquid: Enzymatic Synthesis of Caffeic Acid Phenethyl Ester Analogues from Immature Coffee Beans

Effective neurofibromatosis therapeutics blocking the oncogenic kinase PAK1

A continuous ultrasound‐assisted packed‐bed bioreactor for the lipase‐catalyzed synthesis of caffeic acid phenethyl ester

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