Racemic Fmoc-trans-3-phenylazetidine-2-carboxylic acid
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Racemic Fmoc-trans-3-phenylazetidine-2-carboxylic acid

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Category
Fmoc-Amino Acids
Catalog number
BAT-005720
CAS number
204320-45-6
Molecular Formula
C25H21NO4
Molecular Weight
399.50
Racemic Fmoc-trans-3-phenylazetidine-2-carboxylic acid
IUPAC Name
1-(9H-fluoren-9-ylmethoxycarbonyl)-3-phenylazetidine-2-carboxylic acid
Synonyms
trans-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-3-phenylazetidine-2-carboxylic acid
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Storage
Store at 2-8°C
InChI
InChI=1S/C25H21NO4/c27-24(28)23-21(16-8-2-1-3-9-16)14-26(23)25(29)30-15-22-19-12-6-4-10-17(19)18-11-5-7-13-20(18)22/h1-13,21-23H,14-15H2,(H,27,28)/t21-,23+/m1/s1
InChI Key
SQMOPSBYDIMJRP-GGAORHGYSA-N
Canonical SMILES
C1C(C(N1C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O)C5=CC=CC=C5
1.Analysis of metolachlor ethane sulfonic acid (MESA) chirality in groundwater: A tool for dating groundwater movement in agricultural settings.
Rice CP1, McCarty GW2, Bialek-Kalinski K3, Zabetakis K4, Torrents A4, Hapeman CJ2. Sci Total Environ. 2016 Aug 1;560-561:36-43. doi: 10.1016/j.scitotenv.2016.04.007. Epub 2016 Apr 17.
To better address how much groundwater contributes to the loadings of pollutants from agriculture we developed a specific dating tool for groundwater residence times. This tool is based on metolachlor ethane sulfonic acid, which is a major soil metabolite of metolachlor. The chiral forms of metolachlor ethane sulfonic acid (MESA) and the chiral forms of metolachlor were examined over a 6-year period in samples of groundwater and water from a groundwater-fed stream in a riparian buffer zone. This buffer zone bordered cropland receiving annual treatments with metolachlor. Racemic (rac) metolachlor was applied for two years in the neighboring field, and subsequently S-metolachlor was used which is enriched by 88% with the S-enantiomer. Chiral analyses of the samples showed an exponential increase in abundance of the S-enantiomeric forms for MESA as a function of time for both the first order riparian buffer stream (R(2)=0.80) and for groundwater within the riparian buffer (R(2)=0.
2.A Multi-Enzymatic Cascade Reaction for the Stereoselective Production of γ-Oxyfunctionalyzed Amino Acids.
Enoki J1, Meisborn J1, Müller AC1, Kourist R1. Front Microbiol. 2016 Apr 7;7:425. doi: 10.3389/fmicb.2016.00425. eCollection 2016.
A stereoselective three-enzyme cascade for synthesis of diasteromerically pure γ-oxyfunctionalized α-amino acids was developed. By coupling a dynamic kinetic resolution (DKR) using an N-acylamino acid racemase (NAAAR) and an L-selective aminoacylase from Geobacillus thermoglucosidasius with a stereoselective isoleucine dioxygenase from Bacillus thuringiensis, diastereomerically pure oxidized amino acids were produced from racemic N-acetylamino acids. The three enzymes differed in their optimal temperature and pH-spectra. Their different metal cofactor dependencies led to inhibitory effects. Under optimized conditions, racemic N-acetylmethionine was quantitatively converted into L-methionine-(S)-sulfoxide with 97% yield and 95% de. The combination of these three different biocatalysts allowed the direct synthesis of diastereopure oxyfunctionalized amino acids from inexpensive racemic starting material.
3.A study of the metal binding capacity of saccharinic acids formed during the alkali catalysed decomposition of cellulosic materials: nickel complexation by glucoisosaccharinic acids and xyloisosaccharinic acids.
Almond M1, Belton D1, Humphreys PN2, Laws AP3. Carbohydr Res. 2016 Mar 29;427:48-54. doi: 10.1016/j.carres.2016.03.004. [Epub ahead of print]
The stoichiometry of the metal complexes formed between nickel and the ligand β-glucoisosaccharinic acid (β-GISA) and a racemic mixture of enantiomers of xyloisosaccharinic acid (XISA) has been determined at both neutral and alkaline pHs. Bjerrum plots, Job's plots and conductance measurements indicated that for each of the systems one to one Ni(ligand) complexes were formed at near neutral pHs (<7.5). At intermediate alkaline pHs (7.5-13) there is evidence to support the formation and precipitation of Ni2(ligand)(OH)3 complexes, finally, at high pH (>13) sparingly soluble Ni2(ligand)(OH)4 complexes were formed. The stability constants for the Ni(β-GISA), Ni(α-GISA) and Ni(XISA) complexes formed at neutral pH were determined under identical conditions using polarographic studies. The measured stability constants for Ni(β-GISA) (log10 β = 1.94 ± 0.15) and for Ni(α-GISA)(log10 β = 2.07 ± 0.13) are very similar; the value measured for the Ni(XISA) complex (log10 β = 0.
4.Synthesis of nano-sized stereoselective imprinted polymer by copolymerization of (S)-2-(acrylamido) propanoic acid and ethylene glycol dimethacrylate in the presence of racemic propranolol and copper ion.
Alizadeh T1, Bagherzadeh A2, Shamkhali AN2. Mater Sci Eng C Mater Biol Appl. 2016 Jun 1;63:247-55. doi: 10.1016/j.msec.2016.02.077. Epub 2016 Feb 27.
A new chiral functional monomer of (S)-2-(acrylamido) propanoic acid was obtained by reaction of (l)-alanine with acryloyl chloride. The resulting monomer was characterized by FT-IR and HNMR and then utilized for the preparation of chiral imprinted polymer (CIP). This was carried out by copolymerization of (l)-alanine-derived chiral monomer and ethylene glycol dimethacrylate, in the presence of racemic propranolol and copper nitrate, via precipitation polymerization technique, resulting in nano-sized networked polymer particles. The polymer obtained was characterized by scanning electron microscopy and FT-IR. The non-imprinted polymer was also synthesized and used as blank polymer. Density functional theory (DFT) was also employed to optimize the structures of two diasterometric ternary complexes, suspected to be created in the pre-polymerization step, by reaction of optically active isomers of propranolol, copper ion and (S)-2-(acrylamido) propanoic acid.
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