L-threo-β-Hydroxyaspartic acid
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| Category | Antibiotics |
| Catalog number | BBF-03521 |
| CAS | 7298-98-8 |
| Molecular Weight | 149.10 |
| Molecular Formula | C4H7NO5 |
| Purity | 95% |
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Description
L-threo-β-Hydroxyaspartic acid is an amino acid antibiotic produced by Arthrinium phaeospermum T-53 and Streptomyces sp. 7540-MC1. It has the activity of inhibiting Bacillus subtilis, Xanthomonas oryzae, Mycobacterium phlei and Botrytis cinerea.
Specification
| Synonyms | (3R)-3-hydroxy-L-aspartic acid; Erythro-beta-hydroxy-L-aspartic acid; erythro-beta-Hydroxyaspartic acid; (3R)-3-Hydroxyaspartate |
| IUPAC Name | (2S,3R)-2-amino-3-hydroxybutanedioic acid |
| Canonical SMILES | C(C(C(=O)O)O)(C(=O)O)N |
| InChI | InChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2+/m0/s1 |
| InChI Key | YYLQUHNPNCGKJQ-NHYDCYSISA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 368.7±42.0°C at 760 mmHg |
| Melting Point | 210°C(dec.) |
| Density | 1.7±0.1 g/cm3 |
Reference Reading
1.Potential inhibitors of L-asparagine biosynthesis. 2. Chemistry and biological activity of beta-hydroxyaspartic acid and its derivatives.
Mokotoff M, Bagaglio JF, Parikh BS. J Med Chem. 1975 Apr;18(4):354-8.
Several derivatives of erythro-beta-hydroxy-DL-aspartic acid (1) were prepared as a potential inhibitors of L-asparagine synthetase (ASase) from rat Novikoff hepatoma. Benzylation of 1 gave the dibenzyl ester 2 which upon coupling with carbobenzoxyglycine afforded the blocked dipeptide 3. Deblocking of 3 gave glycl-erythro-beta-hydroxyl-DL-aspartic acid (4) which could not be diazotized. The dimethyl ester of 1 was coupled with carbobenzoxyglycine to give the blocked dipeptide 7a which was deblocked to give dimethyl glycel-erythro-beta-hydroxy-DL-aspartate hydrochloride (8). Diazotization of 8 gave impure diazo compound 9 which on reaction with HCl gave the chloro compound 10. The methods of isolation, assay, and inhibition of ASase are discribed. At 10 mM concentrations 10, 1, and its D and L enantiomers inhibit ASase by 45, 47, 36 and 66 percent, respectively.
2.Insights into the mechanism of Pseudomonas dacunhae aspartate beta-decarboxylase from rapid-scanning stopped-flow kinetics.
Phillips RS1, Lima S, Khristoforov R, Sudararaju B. Biochemistry. 2010 Jun 22;49(24):5066-73. doi: 10.1021/bi100272g.
The mechanism of wild-type and R37A mutant Pseudomonas dacunhae aspartate beta-decarboxylase (ABDC) was studied by rapid-scanning stopped-flow spectrophotometry. Mixing wild-type ABDC with 50 mM disodium l-Asp resulted in the formation of a 325 nm absorption peak within the dead time of the stopped-flow instrument, likely the ketimine of pyridoxamine 5'-phosphate and oxaloacetate or pyruvate. After consumption of the l-Asp, the 360 nm feature of the resting enzyme was restored. Thus, the 325 nm species is a catalytically competent intermediate. In contrast, mixing wild-type ABDC with the disodium salt of either threo- or erythro-beta-hydroxy-dl-Asp at 50 mM resulted in a much slower formation of the 325 nm complex, with an apparent rate constant of approximately 1 or 0.006 s(-1), respectively. When wild-type ABDC is mixed with disodium succinate, a nonreactive analogue of l-Asp, formation of a new peak at 425 nm is observed. The apparent rate constant for formation of the 425 nm band exhibits a hyperbolic dependence on succinate concentration, showing that there is a rapid binding equilibrium, followed by a slower reaction in which the internal aldimine is protonated on the Schiff base N.
3.N-carboxy-anhydrides derived from threo- and erythro-beta-hydroxy-aspartic acids and poly-beta-methyl hydrogen threo-beta-methoxyl-DL-aspartate.
Liwschitz Y, Singerman A. J Chem Soc Perkin 1. 1967;18:1696-700.
4.Oxazolidone derivatives of hydroxyamino acids. V. New synthesis of threo- and erythro-beta-hydroxy-DL-aspartic acids.
Inui T, Ota Y, Ujike T, Katsura H, Kaneko T. Bull Chem Soc Jpn. 1968 Sep;41(9):2148-50.
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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 ╳
