Synthesis of Optically Active Phthaloyld-Aminooxy Acids froml-Amino Acids orl-Hydroxy Acids as Building Blocks for the Preparation of Aminooxy Peptides

2000 ◽  
Vol 65 (22) ◽  
pp. 7667-7675 ◽  
Author(s):  
Injae Shin ◽  
Mung-ryul Lee ◽  
Jiyong Lee ◽  
Mankil Jung ◽  
Weontae Lee ◽  
...  
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Optically Active ◽  
Hydroxy Acids

Biodegradable Polymers Derived from Amino Acids for Biological Applications

2010 ◽  
Vol 76 ◽  
pp. 30-35 ◽  
Author(s):  
Naomi Cohen-Arazi ◽  
Ilanit Hagag ◽  
Michal Kolitz ◽  
Abraham J. Domb ◽  
Jeoshua Katzhendler
Keyword(s):  
Amino Acids ◽  
Molecular Weight ◽  
Ring Opening ◽  
Building Blocks ◽  
Ring Opening Polymerization ◽  
Microwave Assisted Synthesis ◽  
Hydroxy Acids ◽  
Natural Amino Acids ◽  
Direct Condensation ◽  
Positively Charged

Optically active α-hydroxy acids derived from amino acids have been synthesized and polymerized into new biodegradable polyesters. The variety of functional side chains enables the design of positively charged, negatively charged, hydrophobic and hydrophilic chiral building blocks or any combination of these constituents. Hydroxy acids of 15 natural amino acids were prepared with retention of configuration using a straightforward and reliable method of diazotization of α-amino acids. Polyesters were synthesized from these hydroxy acids by a number of methods: direct condensation in bulk, microwave assisted synthesis and ring opening polymerization. The molecular weight of the prepared polymers ranges between 2000 to 5000Da for the direct condensation and the microwave methods, whereas the ring opening polymerization results in high molecular weight polymers (20000 to 30000Da). The polymers were analyzed for their optical activity (Circular Dichroism Spectroscopy), thermal properties (DSC), solubility, molecular weight and polydispersity (GPC), and aqueous degradation. These polymers were tested for their compatibility to neuronal cells growth and differentiation.

scholarly journals One-Pot Biocatalytic Preparation of Enantiopure Unusual α-Amino Acids from α-Hydroxy Acids via a Hydrogen-Borrowing Dual-Enzyme Cascade

Catalysts ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 1470
Author(s):  
Fei Liu ◽  
Junping Zhou ◽  
Meijuan Xu ◽  
Taowei Yang ◽  
Minglong Shao ◽  
...  
Keyword(s):  
Amino Acids ◽  
Mandelic Acid ◽  
Catalytic Efficiency ◽  
Lactobacillus Brevis ◽  
Building Blocks ◽  
Hydroxy Acids ◽  
One Pot ◽  
Diverse Range ◽  
Enzyme Cascade ◽  
Keto Acids

Unusual α-amino acids (UAAs) are important fundamental building blocks and play a key role in medicinal chemistry. Here, we constructed a hydrogen-borrowing dual-enzyme cascade for efficient synthesis of UAAs from α-hydroxy acids (α-HAs). D-mandelate dehydrogenase from Lactobacillus brevis (LbMDH) was screened for the catalysis of α-HAs to α-keto acids but with low activity towards aliphatic α-HAs. Therefore, we rational engineered LbMDH to improve its activity towards aliphatic α-HAs. The substitution of residue Leu243 located in the substrate entrance channel with nonpolar amino acids like Met, Trp, and Ile significantly influenced the enzyme activity towards different α-HAs. Compared with wild type (WT), variant L243W showed 103 U/mg activity towards D-α-hydroxybutyric acid, 1.7 times of the WT’s 60.2 U/mg, while its activity towards D-mandelic acid decreased. Variant L243M showed 2.3 times activity towards D-mandelic acid compared to WT, and its half-life at 40 °C increased to 150.2 h comparing with 98.5 h of WT. By combining LbMDH with L-leucine dehydrogenase from Bacillus cereus, the synthesis of structurally diverse range of UAAs from α-HAs was constructed. We achieved 90.7% conversion for L-phenylglycine production and 66.7% conversion for L-α-aminobutyric acid production. This redox self-sufficient cascade provided high catalytic efficiency and generated pure products.

ChemInform Abstract: Synthesis of Optically Active Phthaloyl D-Aminooxy Acids from L-Amino Acids or L-Hydroxy Acid as Building Blocks for the Preparation of Aminooxy Peptides.

ChemInform ◽  
2001 ◽  
Vol 32 (11) ◽  
pp. no-no
Author(s):  
Injae Shin ◽  
Mung-ryul Lee ◽  
Jiyong Lee ◽  
Mankil Jung ◽  
Weontae Lee ◽  
...  
Keyword(s):  
Amino Acids ◽  
Hydroxy Acid ◽  
Building Blocks ◽  
Optically Active

Artificial Biocatalytic Linear Cascades to Access Hydroxy Acids, Lactones, and α- and β-Amino Acids

Catalysts ◽  
2018 ◽  
Vol 8 (5) ◽  
pp. 205 ◽  
Author(s):  
Joerg Schrittwieser ◽  
Stefan Velikogne ◽  
Wolfgang Kroutil
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Starting Material ◽  
Hydroxy Acids ◽  
Alternative Substrates ◽  
Target Molecules

α-, β-, and ω-Hydroxy acids, amino acids, and lactones represent common building blocks and intermediates for various target molecules. This review summarizes artificial cascades published during the last 10 years leading to these products. Renewables as well as compounds originating from fossil resources have been employed as starting material. The review provides an inspiration for new cascade designs and may be the basis to design variations of these cascades starting either from alternative substrates or extending them to even more sophisticated products.

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