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Cas Database

130622-08-1

130622-08-1

Identification

  • Product Name:D-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, dimethyl ester

  • CAS Number: 130622-08-1

  • EINECS:

  • Molecular Weight:261.275

  • Molecular Formula: C11H19NO6

  • HS Code:

  • Mol File:130622-08-1.mol

Synonyms:

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • 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.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 45 Articles be found

A concise synthesis of (S)-(-)-3-(2-carboxy-4-pyrrolyl)-alanine

Adamczyk, Maciej,Johnson, Donald D.,Reddy, Rajarathnam E.

, p. 3063 - 3068 (2000)

A convergent synthesis of (S)-(-)-3-(2-carboxy-4-pyrrolyl)-alanine (CPA) 1, a non-proteinogenic amino acid is described starting from a commercially available dimethyl L-aspartate 2 in good overall yield. Copyright (C) 2000 Elsevier Science Ltd.

Visualizing the reaction cycle in an Iron(II)- and 2-(Oxo)-glutarate-dependent hydroxylase

Mitchell, Andrew J.,Dunham, Noah P.,Martinie, Ryan J.,Bergman, Jonathan A.,Pollock, Christopher J.,Hu, Kai,Allen, Benjamin D.,Chang, Wei-Chen,Silakov, Alexey,Bollinger, J. Martin,Krebs, Carsten,Boal, Amie K.

, p. 13830 - 13836 (2017)

Iron(II)- and 2-(oxo)-glutarate-dependent oxygenases catalyze diverse oxidative transformations that are often initiated by abstraction of hydrogen from carbon by iron(IV)-oxo (ferryl) complexes. Control of the relative orientation of the substrate C-H and ferryl Fe-O bonds, primarily by direction of the oxo group into one of two cisrelated coordination sites (termed inline and offline), may be generally important for control of the reaction outcome. Neither the ferryl complexes nor their fleeting precursors have been crystallographically characterized, hindering direct experimental validation of the offline hypothesis and elucidation of the means by which the protein might dictate an alternative oxo position. Comparison of high-resolution X-ray crystal structures of the substrate complex, an Fe(II)-peroxysuccinate ferryl precursor, and a vanadium(IV)-oxo mimic of the ferryl intermediate in the L-arginine 3-hydroxylase, VioC, reveals coordinated motions of active site residues that appear to control the intermediate geometries to determine reaction outcome.

A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor

Fanning, Kate N.,Sutherland, Andrew

, p. 8479 - 8481 (2007)

A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H2-receptor, has been developed in 10 steps and in 31% overall yield from l-aspartic acid. The key steps involved a two-carbon homologation of an l-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative.

Geometric changes around an N atom due to a urethane-type bis(tert-butoxycarbonyl) substituent

Wojewska, Dominika,Kluczyk, Alicja,Slepokura, Katarzyna

, p. 82 - 86 (2013)

Two crystal structures of urethane-protected derivatives of aspartic acid dimethyl ester are presented, namely dimethyl (2S)-2-[(tert-butoxycarbonyl) amino]butanedioate, C11H19NO6, and dimethyl (2S)-2-{bis[(tert-butoxycarbonyl]amino}butanedioate, C16H 27NO8. The geometry at the N atom is discussed and compared with similar structures. The analysis of singly and doubly N-substituted derivatives reveals an elongation of all bonds involving the N atom and conformational changes of the amino acid side chain due to steric interactions with two bulky substituents on the amino group.

A short and efficient synthesis of (S)-(+)-2-(Hydroxymethyl)-6-piperidin-2- one

Upadhyay, Puspesh K.,Kumar, Pradeep

, p. 2512 - 2514 (2010)

A concise synthesis of (S)-(+)-2-(hydroxymethyl)-6-piperidin-2-one is described that employs l-aspartic acid as chiral pool starting material and Wittig reaction as the key step. Georg Thieme Verlag Stuttgart - New York.

Total synthesis of a pyrrole lactone alkaloid, longanlactone

Reddy, Chada Raji,Reddy, Motatipally Damoder,Dilipkumar, Uredi

, p. 6310 - 6313 (2014)

The first asymmetric total synthesis of the natural pyrrole lactone longanlactone has been achieved. The key reactions, a Barbier propargylation and a Paal-Knorr pyrrole synthesis, have provided easy access to the target natural product from L-aspartic acid in six steps and 31 % overall yield. The C-4 epimer of the natural product and propionyllonganlactone have also been prepared by this strategy.

Substrate Engineering in Lipase-Catalyzed Selective Polymerization of d -/ l -Aspartates and Diols to Prepare Helical Chiral Polyester

Zhang, Yu,Xia, Bo,Li, Yanyan,Lin, Xianfu,Wu, Qi

, p. 918 - 926 (2021)

The synthesis of optically pure polymers is one of the most challenging tasks in polymer chemistry. Herein, Novozym 435 (Lipase B from Candida antarctica, immobilized on Lewatit VP OC 1600)-catalyzed polycondensation between d-/l-aspartic acid (Asp) diester and diols for the preparation of helical chiral polyesters was reported. Compared with d-Asp diesters, the fast-reacting l-Asp diesters easily reacted with diols to provide a series of chiral polyesters containing N-substitutional l-Asp repeating units. Besides amino acid configuration, N-substituent side chains and the chain length of diols were also investigated and optimized. It was found that bulky acyl N-substitutional groups like N-Boc and N-Cbz were more favorable for this polymerization than small ones probably due to competitively binding of these small acyl groups into the active site of Novozym 435. The highest molecular weight can reach up to 39.5 × 103 g/mol (Mw, D = 1.64). Moreover, the slow-reacting d-Asp diesters were also successfully polymerized by modifying the substrate structure to create a "nonchiral"condensation environment artificially. These enantiocomplementary chiral polyesters are thermally stable and have specific helical structures, which was confirmed by circular dichroism (CD) spectra, scanning electron microscope (SEM), and molecular calculation.

Selective, Modular Probes for Thioredoxins Enabled by Rational Tuning of a Unique Disulfide Structure Motif

Becker, Katja,Busker, Sander,Felber, Jan G.,Maier, Martin S.,Poczka, Lena,Scholzen, Karoline,Theisen, Ulrike,Thorn-Seshold, Julia,Thorn-Seshold, Oliver,Zeisel, Lukas,Arnér, Elias S. J.,Brandst?dter, Christina

supporting information, p. 8791 - 8803 (2021/06/27)

Specialized cellular networks of oxidoreductases coordinate the dithiol/disulfide-exchange reactions that control metabolism, protein regulation, and redox homeostasis. For probes to be selective for redox enzymes and effector proteins (nM to μM concentrations), they must also be able to resist non-specific triggering by the ca. 50 mM background of non-catalytic cellular monothiols. However, no such selective reduction-sensing systems have yet been established. Here, we used rational structural design to independently vary thermodynamic and kinetic aspects of disulfide stability, creating a series of unusual disulfide reduction trigger units designed for stability to monothiols. We integrated the motifs into modular series of fluorogenic probes that release and activate an arbitrary chemical cargo upon reduction, and compared their performance to that of the literature-known disulfides. The probes were comprehensively screened for biological stability and selectivity against a range of redox effector proteins and enzymes. This design process delivered the first disulfide probes with excellent stability to monothiols yet high selectivity for the key redox-Active protein effector, thioredoxin. We anticipate that further applications of these novel disulfide triggers will deliver unique probes targeting cellular thioredoxins. We also anticipate that further tuning following this design paradigm will enable redox probes for other important dithiol-manifold redox proteins, that will be useful in revealing the hitherto hidden dynamics of endogenous cellular redox systems.

Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine

Sch?del, Nicole,Icik, Esra,Martini, Maike,Altevogt, Luca,Ramming, Isabell,Greulich, Andreas,Baro, Angelika,Bilitewski, Ursula,Laschat, Sabine

supporting information, p. 2260 - 2268 (2021/03/04)

Amino acid derivatives with a central cationic heterocyclic core (e.g., imidazolium) are biologically relevant cross-linkers of proteins and advanced glycation end (AGE) products. Here, imidazolium-containing cross-linkers were synthesized from imidazole or histidine by N-alkylation employing aspartate- and glutamate-derived mesylates as key step. Biological investigations were carried out to probe the biocompatibility of these compounds.

Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers

Agelidis, Nektarios,Altevogt, Luca,Baro, Angelika,Bilitewski, Ursula,Bugdayci, Bakiye,Icik, Esra,Jolly, Anthony,L?ffler, Paul,Laschat, Sabine

supporting information, (2020/09/01)

Three N-Boc-protected amino acids, l-serine, l-aspartic, and l-glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann-Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu-catalyzed click reaction provided a library of amino acid based triazoles, which were further N-methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).

Selenolysine: A New Tool for Traceless Isopeptide Bond Formation

Dardashti, Rebecca Notis,Kumar, Shailesh,Sternisha, Shawn M.,Reddy, Post Sai,Miller, Brian G.,Metanis, Norman

supporting information, p. 4952 - 4957 (2020/04/07)

Despite their biological importance, post-translationally modified proteins are notoriously difficult to produce in a homogeneous fashion by using conventional expression systems. Chemical protein synthesis or semisynthesis offers a solution to this problem; however, traditional strategies often rely on sulfur-based chemistry that is incompatible with the presence of any cysteine residues in the target protein. To overcome these limitations, we present the design and synthesis of γ-selenolysine, a selenol-containing form of the commonly modified proteinogenic amino acid, lysine. The utility of γ-selenolysine is demonstrated with the traceless ligation of the small ubiquitin-like modifier protein, SUMO-1, to a peptide segment of human glucokinase. The resulting polypeptide is poised for native chemical ligation and chemoselective deselenization in the presence of unprotected cysteine residues. Selenolysine's straightforward synthesis and incorporation into synthetic peptides marks it as a universal handle for conjugating any ubiquitin-like modifying protein to its target.

Process route upstream and downstream products

Process route

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

(S)-2-(tert-butoxycarbonylamino)-1,4-butanediol
128427-10-1,156627-42-8

(S)-2-(tert-butoxycarbonylamino)-1,4-butanediol

Conditions
Conditions Yield
L-glutamic acid dimethyl ester
6525-53-7,16422-27-8,40149-68-6

L-glutamic acid dimethyl ester

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate
59279-60-6,130622-05-8,861658-15-3

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
94%
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

dimethyl L-aspartate hydrochloride
32213-95-9

dimethyl L-aspartate hydrochloride

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
With sodium hydrogencarbonate; In dichloromethane; water; for 4h;
90%
dimethyl L-aspartate hydrochloride; With triethylamine; In acetonitrile;
di-tert-butyl dicarbonate; In acetonitrile; for 9h;
89%
With triethylamine; In methanol; at -78 - 20 ℃; for 18h;
78%
With triethylamine; In dichloromethane; for 3h; Ambient temperature;
10.3 g
With triethylamine; In tetrahydrofuran; at 20 ℃; for 2.5h;
With triethylamine; In methanol; at 20 ℃; for 23h;
2.09 g
With triethylamine; In dichloromethane;
With triethylamine; In dichloromethane; at 0 - 20 ℃; for 10.25h; Inert atmosphere;
With dmap; tetraethyl ammonium; In dichloromethane; at 20 ℃;
methanol
67-56-1

methanol

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
methanol; L-Aspartic acid; With chloro-trimethyl-silane; at 0 - 20 ℃; for 25h; Inert atmosphere;
di-tert-butyl dicarbonate; With triethylamine; for 2h; Inert atmosphere;
100%
methanol; L-Aspartic acid; With chloro-trimethyl-silane; at 0 - 20 ℃; for 48h;
di-tert-butyl dicarbonate; With triethylamine; at 20 ℃; for 21h;
96%
methanol; L-Aspartic acid; With thionyl chloride; at 0 - 20 ℃; for 14h; Inert atmosphere;
di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In dichloromethane; water; for 4h; Reflux;
92%
methanol; L-Aspartic acid; With chloro-trimethyl-silane;
di-tert-butyl dicarbonate; With triethylamine; Further stages.;
91%
methanol; L-Aspartic acid; With thionyl chloride; at 60 ℃; for 6h; Inert atmosphere;
di-tert-butyl dicarbonate; With sodium carbonate; In tetrahydrofuran; water; at 4 - 25 ℃; for 24.5h; Inert atmosphere;
87%
methanol; L-Aspartic acid; With chloro-trimethyl-silane; at 0 - 20 ℃; for 18h; Inert atmosphere;
di-tert-butyl dicarbonate; With triethylamine; at 0 - 20 ℃; for 4h;
82%
methanol; L-Aspartic acid; With chloro-trimethyl-silane; at 0 - 20 ℃; for 14h; Inert atmosphere;
di-tert-butyl dicarbonate; In methanol;
80%
methanol; L-Aspartic acid; With chloro-trimethyl-silane; at 0 - 20 ℃; for 23h;
di-tert-butyl dicarbonate; With triethylamine; at 0 - 20 ℃; for 23h;
67%
methanol; L-Aspartic acid; With thionyl chloride; at 0 ℃; for 2h; Reflux;
di-tert-butyl dicarbonate; With triethylamine; In dichloromethane; at 20 ℃; for 8h;
methanol; L-Aspartic acid; With chloro-trimethyl-silane; at 0 - 20 ℃; for 16h;
di-tert-butyl dicarbonate; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h;
methanol; L-Aspartic acid; With chloro-trimethyl-silane; at 0 - 20 ℃; for 16h; Inert atmosphere;
di-tert-butyl dicarbonate; With triethylamine; In methanol; at 0 - 20 ℃; for 16h;
Boc-Asp-OH
13726-67-5

Boc-Asp-OH

methyl iodide
74-88-4

methyl iodide

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
With sodium chloride; potassium carbonate; In water;
99%
Boc-Asp-OH; With potassium carbonate; In N,N-dimethyl-formamide; for 0.166667h; Inert atmosphere; Cooling with ice;
methyl iodide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1.5h; Inert atmosphere;
8.5 g
dimethyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}butanedioate
219617-08-0

dimethyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}butanedioate

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
With lithium bromide; In acetonitrile; at 65 ℃; for 10h;
97%
With bismuth(III) bromide; water; In acetonitrile; at 20 ℃; for 2h;
94%
With montmorillonite K-10; In toluene; at 65 ℃; for 0.5h;
93%
With indium; In methanol; for 18h; Heating;
90%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
chloro-trimethyl-silane; L-Aspartic acid; In methanol; at 0 - 20 ℃; for 16h;
di-tert-butyl dicarbonate; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h;
L-Aspartic acid dimethyl ester
6384-18-5

L-Aspartic acid dimethyl ester

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
With sodium carbonate; In 1,4-dioxane; Yield given;
With triethylamine; In 1,4-dioxane; water; at 0 ℃; for 2h;
With triethylamine; In methanol; Yield given;
With triethylamine; In methanol;
With triethylamine;
With triethylamine; In methanol; at 20 ℃;
With sodium hydrogencarbonate; In dichloromethane; water; for 4h; Reflux;
9.08 g
With triethylamine; at 0 - 20 ℃; for 4h; Inert atmosphere;
L-Aspartic acid dimethyl ester; With triethylamine; at 0 ℃; for 0.166667h; pH=>8;
di-tert-butyl dicarbonate; at 20 ℃; for 4h;
In 1,4-dioxane; water; at 50 ℃; for 5h;
16.4 g
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
With thionyl chloride; sodium hydrogencarbonate; In methanol; water; ethyl acetate;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

dimethyl (R)-2-aminobutanedioate hydrochloride
14358-33-9,32213-95-9,69630-50-8

dimethyl (R)-2-aminobutanedioate hydrochloride

(2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester
130622-08-1

(2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester

dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

Conditions
Conditions Yield
94%

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