D-Aspartic acid,3-hydroxy-, (3R)-rel-
- CAS Number:4294-45-5
- Molecular Formula:C4H7NO5
- Molecular Weight:149.103
- Mol File:4294-45-5.mol
Synonyms:Asparticacid, 3-hydroxy-, DL-threo- (8CI);DL-Aspartic acid, 3-hydroxy-, threo-;DL-threo-3-Hydroxyaspartic acid;threo-3-Hydroxy-DL-asparticacid;
Physicochemical Properties
- Melting Point:>230 °C
- Boiling Point:368.7 °C at 760 mmHg
- Density:1.738 g/cm3
- Solubility:N/A
- Flash Point:176.8 °C
- Vapor Density:N/A
- Refractive Index:1.583
- Sensitive:N/A
- Storage Temp.:−20°C
- Appearance/Colour:off-white solid
D-Aspartic acid,3-hydroxy-, (3R)-rel- Safety information and MSDS
·Hazard identification:
| Pictogram(s) | no data available |
|---|---|
| Signal word | no data available |
| Hazard statement(s) | no data available |
| Precautionary statement(s) | |
| Prevention | no data available |
| Response | no data available |
| Storage | no data available |
| Disposal | no data available |
·Composition/information on ingredients:
| Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
|---|---|---|---|---|
| D,L-threo-β-Hydroxy Aspartic Acid | D,L-threo-β-Hydroxy Aspartic Acid | 4294-45-5 | none | 100% |
·First-aid measures:
General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
·Fire-fighting measures:
Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.
·Accidental release measures:
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.
D-Aspartic acid,3-hydroxy-, (3R)-rel- Relevant articles
All total 22 Articles be found
All total 22 Articles be foundStalobacin: Discovery of Novel Lipopeptide Antibiotics with Potent Antibacterial Activity against Multidrug-Resistant Bacteria
Matsui, Kouhei,Matsui, Kouhei,Kan, Yukiko,Kikuchi, Junko,Matsushima, Keisuke,Takemura, Miki,Maki, Hideki,Kozono, Iori,Ueda, Taichi,Minagawa, Kazuyuki
supporting information, p. 6090 - 6095 (2020/07/10)
A novel lipopeptide antibiotic, stalobacin I (1), was discovered from a culture broth of an unidentified Gram-negative bacterium. Stalobacin I (1) had a unique chemical architecture composed of an upper and a lower half peptide sequence, which were linked via a hemiaminal methylene moiety. The sequence of 1 contained an unusual amino acid, carnosadine, 3,4-dihydroxyariginine, 3-hydroxyisoleucine, and 3-hydroxyaspartic acid, and a novel cyclopropyl fatty acid. The antibacterial activity of 1 against a broad range of drug-resistant Gram-positive bacteria was much stronger than those of "last resort"antibiotics such as vancomycin, linezolid, and telavancin (MIC 0.004-0.016 μg/mL). Furthermore, compound 1 induced a characteristic morphological change in Gram-positive and Gram-negative strains by inflating the bacterial cell body. The absolute configuration of a cyclopropyl amino acid, carnosadine, was determined by the synthetic study of its stereoisomers, which was an essential component for the strong activity of 1.
Rapid chemoenzymatic route to glutamate transporter inhibitor l-TFB-TBOA and related amino acids
Fu, Haigen,Younes, Sabry H. H.,Saifuddin, Mohammad,Tepper, Pieter G.,Zhang, Jielin,Keller, Erik,Heeres, André,Szymanski, Wiktor,Poelarends, Gerrit J.
supporting information, p. 2341 - 2344 (2017/03/20)
The complex amino acid (l-threo)-3-[3-[4-(trifluoromethyl)benzoylamino]benzyloxy]aspartate (l-TFB-TBOA) and its derivatives are privileged compounds for studying the roles of excitatory amino acid transporters (EAATs) in regulation of glutamatergic neurotransmission, animal behavior, and in the pathogenesis of neurological diseases. The wide-spread use of l-TFB-TBOA stems from its high potency of EAAT inhibition and the lack of off-target binding to glutamate receptors. However, one of the main challenges in the evaluation of l-TFB-TBOA and its derivatives is the laborious synthesis of these compounds in stereoisomerically pure form. Here, we report an efficient and step-economic chemoenzymatic route that gives access to enantio- and diastereopure l-TFB-TBOA and its derivatives at multigram scale.
Poecillastrin E, F, and G, cytotoxic chondropsin-type macrolides from a marine sponge Poecillastra sp.
Irie, Raku,Hitora, Yuki,Ise, Yuji,Okada, Shigeru,Takada, Kentaro,Matsunaga, Shigeki
, p. 1430 - 1434 (2018/02/13)
Poecillastrin E (1), F (2), and G (3) were isolated from a marine sponge Poecillastra sp. as the cytotoxic constituents. Their planar structures were determined by analyzing the MS and NMR spectra. They are closely related to the known poecillastrin C (4). The absolute configuration of the β-hydroxyaspartic acid (OHAsp) residue was determined to be D-threo by Marfey's analysis of the hydrolysate. The mode of lactone ring formation of OHAsp residue in 1–3 was determined by selective reduction of the ester linkage followed by acid hydrolysis.
Isolation and amino acid sequence of a dehydratase acting on D-erythro-3- hydroxyaspartate from Pseudomonas sp. N99, and its application in the production of optically active 3-hydroxyaspartate
Nagano, Hiroyuki,Shibano, Kana,Matsumoto, Yu,Yokota, Atsushi,Wada, Masaru
, p. 1156 - 1164 (2017/05/29)
An enzyme catalyzing the ammonia-lyase reaction for the conversion of D-erythro-3-hydroxyaspartate to oxaloacetate was purified from the cell-free extract of a soil-isolated bacterium Pseudomonas sp. N99. The enzyme exhibited ammonia-lyase activity toward L-threo-3-hydroxyaspartate and D-erythro-3- hydroxyaspartate, but not toward other 3-hydroxyaspartate isomers. The deduced amino acid sequence of the enzyme, which belongs to the serine/ threonine dehydratase family, shows similarity to the sequence of L-threo-3-hydroxyaspartate ammonia- lyase (EC 4.3.1.16) from Pseudomonas sp. T62 (74%) and Saccharomyces cerevisiae (64%) and serine racemase from Schizosaccharomyces pombe (65%). These results suggest that the enzyme is similar to L-threo-3-hydroxyaspartate ammonia-lyase from Pseudomonas sp. T62, which does not act on D-erythro-3-hydroxyaspartate. We also then used the recombinant enzyme expressed in Escherichia coli to produce optically pure L-erythro-3-hydroxyaspartate and D-threo-3-hydroxyaspartate from the corresponding DL-racemic mixtures. The enzymatic resolution reported here is one of the simplest and the first enzymatic method that can be used for obtaining optically pure L-erythro-3-hydroxyaspartate.
Ambiguity of NRPS Structure Predictions: Four Bidentate Chelating Groups in the Siderophore Pacifibactin
Hardy, Clifford D.,Butler, Alison
, p. 990 - 997 (2019/03/26)
Identified through a bioinformatics approach, a nonribosomal peptide synthetase gene cluster in Alcanivorax pacificus encodes the biosynthesis of the new siderophore pacifibactin. The structure of pacifibactin differs markedly from the bioinformatic prediction and contains four bidentate metal chelation sites, atypical for siderophores. Genome mining and structural characterization of pacifibactin is reported herein, as well as characterization of pacifibactin variants accessible due to a lack of adenylation domain fidelity during biosynthesis. A spectrophotometric titration of pacifibactin with Fe(III) and 13C NMR spectroscopy of the Ga(III)-pacifibactin complex establish 1:1 metal:pacifibactin coordination and reveal which of the bidentate binding groups are coordinated to the metal. The photoreaction of Fe(III)-pacifibactin, resulting from Fe(III) coordination of the β-hydroxyaspartic acid ligands, is reported.
D-Aspartic acid,3-hydroxy-, (3R)-rel- Synthetic route And Reaction conditions
- 110-16-7,26099-09-2
maleic acid
- 4294-45-5
DL-threo-β-hydroxyaspartic acid
| Conditions | Yield |
|---|---|
- 4294-45-5
DL-threo-β-hydroxyaspartic acid
- 1186-90-9,1860-87-3,4294-45-5,5174-55-0,5753-30-0,6532-76-9,7298-98-8,7298-99-9,16417-36-0,71653-06-0,81601-40-3
erythro-β-hydroxy-DL-aspartic acid
| Conditions | Yield |
|---|---|
Withhydrogenchloride; |
- 4294-45-5
DL-threo-β-hydroxyaspartic acid
| Conditions | Yield |
|---|---|
Multistep reaction;
(i) SOCl2, (ii) aq. HCl; |
- 16533-72-5,51274-37-4
cis-2,3-epoxysuccinic acid
- 4294-45-5
DL-threo-β-hydroxyaspartic acid
| Conditions | Yield |
|---|---|
Withammonium hydroxide; |
| Conditions | Yield |
|---|---|
Multistep reaction;
(i) aq. NaOH, MeOH, (ii) aq. HCl; |
- 71653-06-0
3-hydroxyaspartic acid
- 4294-45-5
DL-threo-β-hydroxyaspartic acid
| Conditions | Yield |
|---|---|
Withwater;
at 125 ℃; |
- 7403-74-9,19071-25-1,21788-47-6,74841-95-5,112335-64-5
lower-melting inactive 3-chloro-2-hydroxy-succinic acid
- 71653-06-0
3-hydroxyaspartic acid
- 4294-45-5
DL-threo-β-hydroxyaspartic acid
| Conditions | Yield |
|---|---|
- 4294-45-5
DL-threo-β-hydroxyaspartic acid
| Conditions | Yield |
|---|---|
Chloraepfelsaeure, NH3 <7d, 100grad>, Abtrennung v. erythro-form d. Ionenaustauscher; | |
Benzylamin-Salz der (+-)-threo-3-Benzylamino-2-hydroxy-bernsteinsaeure, 5-stdg. Hydrierung an Pd/Norit in Eg. bei 70-80grad; |
- 110-17-8,26099-09-2
(2E)-but-2-enedioic acid
- 1186-90-9,1860-87-3,4294-45-5,5174-55-0,5753-30-0,6532-76-9,7298-98-8,7298-99-9,16417-36-0,71653-06-0,81601-40-3
erythro-β-hydroxy-DL-aspartic acid
| Conditions | Yield |
|---|---|
- 19372-03-3,66619-94-1,88419-27-6,136205-62-4,136314-88-0
aziridine-2,3-dicarboxylic acid diethyl ester
- 1186-90-9,1860-87-3,4294-45-5,5174-55-0,5753-30-0,6532-76-9,7298-98-8,7298-99-9,16417-36-0,71653-06-0,81601-40-3
erythro-β-hydroxy-DL-aspartic acid
| Conditions | Yield |
|---|---|
Multistep reaction;
(i) aq. HClO4, (ii) aq. HCl; |
D-Aspartic acid,3-hydroxy-, (3R)-rel- Raw materials
- 71653-06-0
3-hydroxyaspartic acid
- 7403-74-9
lower-melting inactive 3-chloro-2-hydroxy-succinic acid
- 2706-75-4
sodium glyoxylate
- 6463-75-8
N-(DL-α-Methyl-benzyl)-threo-β-hydroxy-DL-asparaginsaeure
- 110-16-7
maleic acid
D-Aspartic acid,3-hydroxy-, (3R)-rel- Target Products
Business Type:
- Lab/Research institutionsTrading CompanyManufacturers
Certificate:
- Product LicenseEnterprise AuthenticationISOGMPFDAHALAL
Country :
China (Mainland)(16)
United Kingdom(1)
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