L-Phenyllactic acid
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| Category | Others |
| Catalog number | BBF-04752 |
| CAS | 20312-36-1 |
| Molecular Weight | 166.2 |
| Molecular Formula | C9H10O3 |
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Description
A building block used in the synthesis of peptidomimetics as neuropeptide S receptor agonists.
Specification
| Synonyms | L-3-phenyllactic acid |
| IUPAC Name | (2S)-2-hydroxy-3-phenylpropanoic acid |
| Canonical SMILES | C1=CC=C(C=C1)CC(C(=O)O)O |
| InChI | InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/m0/s1 |
| InChI Key | VOXXWSYKYCBWHO-QMMMGPOBSA-N |
Properties
| Appearance | White powder |
| Boiling Point | 331.6 ℃ at 760 mmHg |
| Melting Point | 121-125 ℃ |
| Density | 1.265 g/cm3 |
| LogP | 0.67460 |
Reference Reading
1. Three new tyrosol derivatives from Huangjing wine
Yan-Bin Ren, Xing-Wen Wang, Jia-Xuan Bai, Chang Liu, Si-Lin Yu, Yue Zhou, Cong-Cong Lin, Da-Hong Yao, Jian Huang, Jin-Hui Wang J Asian Nat Prod Res. 2022 Nov;24(11):1018-1024. doi: 10.1080/10286020.2021.2008371. Epub 2021 Nov 29.
Phytochemical investigation on the concentrate of Huangjing wine, resulted in the isolation of three new tyrosol derivatives 4'''-hydroxyphenethyl 2-(R)-hydroxy-3-phenylpropionate (1), 4'''-hydroxyphenethyl(4'-hydroxy-3'-methoxyphenyl)propionate (2) and 4''-hydroxyphenethyl ethyl succinate (3), together with 5 known compounds, ferulic acid (4), L-phenyllactic acid (5), hydroxytyrosol (6), dihydroferulic acid (7), cyclo(L-Pro-D-Tyr) (8). Their structures were elucidated using spectroscopic analysis and by comparison with the literature data. All compounds displayed antioxidant effect in the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical. Among them, the new compound 2 exhibited obvious antioxidant effect, and new compounds 1 and 3 exhibited medium antioxidant effect.
2. [Expression of a Lactobacillus casei L-lactate dehydrogenase mutant in Pichia pastoris for asymmetric reduction of phenylpyruvate]
Ting Zhang, Jianfang Li, Die Hu, Chuang Li, Bochun Hu, Minchen Wu Sheng Wu Gong Cheng Xue Bao. 2020 May 25;36(5):959-968. doi: 10.13345/j.cjb.190383.
To improve the productivity of L-phenyllactic acid (L-PLA), L-LcLDH1(Q88A/I229A), a Lactobacillus casei L-lactate dehydrogenase mutant, was successfully expressed in Pichia pastoris GS115. An NADH regeneration system in vitro was then constructed by coupling the recombinant (re) LcLDH1(Q88A/I229A) with a glucose 1-dehydrogenase for the asymmetric reduction of phenylpyruvate (PPA) to L-PLA. SDS-PAGE analysis showed that the apparent molecular weight of reLcLDH1(Q88A/I229A) was 36.8 kDa. And its specific activity was 270.5 U/mg, 42.9-fold higher than that of LcLDH1 (6.3 U/mg). The asymmetric reduction of PPA (100 mmol/L) was performed at 40 °C and pH 5.0 in an optimal biocatalytic system, containing 10 U/mL reLcLDH1(Q88A/I229A), 1 U/mL SyGDH, 2 mmol/L NAD⁺ and 120 mmol/L D-glucose, producing L-PLA with 99.8% yield and over 99% enantiomeric excess (ee). In addition, the space-time yield (STY) and average turnover frequency (aTOF) were as high as 9.5 g/(L·h) and 257.0 g/(g·h), respectively. The high productivity of reLcLDH1(Q88A/I229A) in the asymmetric reduction of PPA makes it a promising biocatalyst in the preparation of L-PLA.
3. Enantioselective Biosynthesis of L-Phenyllactic Acid From Phenylpyruvic Acid In Vitro by L-Lactate Dehydrogenase Coupling With Glucose Dehydrogenase
Dong Zhang, Ting Zhang, Yuqing Lei, Wenqian Lin, Xingyi Chen, Minchen Wu Front Bioeng Biotechnol. 2022 Feb 18;10:846489. doi: 10.3389/fbioe.2022.846489. eCollection 2022.
As a valuable versatile building block, L-phenyllactic acid (L-PLA) has numerous applications in the fields of agriculture, pharmaceuticals, and biodegradable plastics. However, both normally chemically synthesized and naturally occurring PLA are racemic, and the production titer of L-PLA is not satisfactory. To improve L-PLA production and reduce the high cost of NADH, an in vitro coenzyme regeneration system of NADH was achieved using the glucose dehydrogenase variant LsGDHD255C and introduced into the L-PLA production process. Here an NADH-dependent L-lactate dehydrogenase-encoding variant gene (L-Lcldh1Q88A/I229A) was expressed in Pichia pastoris GS115. The specific activity of L-LcLDH1Q88A/I229A (Pp) was as high as 447.6 U/mg at the optimum temperature and pH of 40°C and 5.0, which was 38.26-fold higher than that of wild-type L-LcLDH1 (Pp). The catalytic efficiency (k cat/K m) of L-LcLDH1Q88A/I229A (Pp) was 94.3 mM-1 s-1, which was 67.4- and 25.5-fold higher than that of L-LcLDH1(Pp) and L-LcLDH1Q88A/I229A (Ec) expressed in Escherichia coli, respectively. Optimum reactions of L-PLA production by dual-enzyme catalysis were at 40°C and pH 5.0 with 10.0 U/ml L-LcLDH1Q88A/I229A (Pp) and 4.0 U/ml LsGDHD255C. Using 0.1 mM NAD+, 400 mM (65.66 g/L) phenylpyruvic acid was completely hydrolyzed by fed-batch process within 6 h, affording L-PLA with 90.0% yield and over 99.9% ee p. This work would be a promising technical strategy for the preparation of L-PLA at an industrial scale.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
