N-Benzoylserinol
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| Category | Others |
| Catalog number | BBF-05232 |
| CAS | 138625-63-5 |
| Molecular Weight | 195.21 |
| Molecular Formula | C10H13NO3 |
| Purity | >95% by HPLC |
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Specification
| Synonyms | Bz-DL-Ser-ol; N-[2-hydroxy-1-(hydroxymethyl)ethyl]benzamide; 2-(Benzoylamino)-1,3-propanediol; 2-benzoylamino-1,3-propyleneglycol; N-(β,β'-dihydroxy-isopropyl)-benzamide; 2-(N-benzoylamino)-1,3-propanediol |
| Storage | Store at -20°C |
| IUPAC Name | N-(1,3-dihydroxypropan-2-yl)benzamide |
| Canonical SMILES | C1=CC=C(C=C1)C(=O)NC(CO)CO |
| InChI | InChI=1S/C10H13NO3/c12-6-9(7-13)11-10(14)8-4-2-1-3-5-8/h1-5,9,12-13H,6-7H2,(H,11,14) |
| InChI Key | HPJXHEKSMWBVRG-UHFFFAOYSA-N |
Properties
| Boiling Point | 501.8±40.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Reactions of O-acyl-L-serines with tryptophanase, tyrosine phenol-lyase, and tryptophan synthase
R S Phillips Arch Biochem Biophys. 1987 Jul;256(1):302-10. doi: 10.1016/0003-9861(87)90450-4.
The reactions of tryptophanase, tyrosine phenol-lyase, and tryptophan synthase with a new class of substrates, the O-acyl-L-serines, have been examined. A method for preparation of O-benzoyl-L-serine in high yield from tert.-butyloxycarbonyl (tBoc)-L-serine has been developed. Reaction of the cesium salt of tBoc-L-serine with benzyl bromide in dimethylformamide gives tBoc-L-serine benzyl ester in excellent yield. Acylation with benzoyl chloride and triethylamine in acetonitrile followed by hydrogenolysis with 10% palladium on carbon in trifluoroacetic acid gives O-benzoyl-L-serine, isolated as the hydrochloride salt. O-Benzoyl-L-serine is a good substrate for beta-elimination or beta-substitution reactions catalyzed by both tryptophanase and tyrosine phenol-lyase, with Vmax values 5- to 6-fold those of the physiological substrates and comparable to that of S-(o-nitrophenyl)-L-cysteine. Unexpectedly, O-acetyl-L-serine is a very poor substrate for these enzymes, with Vmax values about 5% of those of the physiological substrates. Both O-acyl-L-serines are poor substrates for tryptophan synthase, measured either by the synthesis of 5-fluoro-L-tryptophan from 5-fluoroindole and L-serine catalyzed by the intact alpha 2 beta 2 subunit or by the beta-elimination reaction catalyzed by the isolated beta 2 subunit. With all three enzymes, the elimination of benzoate appears to be irreversible. These results suggest that the binding energy from the aromatic ring of O-benzoyl-L-serine is used to lower the transition-state barrier for the elimination reactions catalyzed by tryptophanase and tyrosine phenol-lyase. Our findings support the suggestion (M. N. Kazarinoff and E. E. Snell (1980) J. Biol. Chem. 255, 6228-6233) that tryptophanase undergoes a conformational change during catalysis and suggest that tyrosine phenol-lyase also may undergo a conformational change during catalysis.
2. Enterobactin: the characteristic catecholate siderophore of Enterobacteriaceae is produced by Streptomyces species.(1)
H P Fiedler, P Krastel, J Müller, K Gebhardt, A Zeeck FEMS Microbiol Lett. 2001 Mar 15;196(2):147-51. doi: 10.1111/j.1574-6968.2001.tb10556.x.
Enterobactin is described in the literature as the typical iron-chelating compound (siderophore) produced by bacteria of the family Enterobacteriaceae. In the course of a HPLC with diode array detection screening programme for detection of novel secondary metabolites, enterobactin, its biosynthetic precursor 2,3-dihydroxy-N-benzoylserine and its linear dimer and trimer condensation products were found to be produced by two Streptomyces strains besides the trihydroxamate-type siderophores desferri-ferrioxamine B and E.
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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 ╳
