L-Asparagine tert-butyl ester
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L-Asparagine tert-butyl ester

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Category
L-Amino Acids
Catalog number
BAT-003965
CAS number
25456-86-4
Molecular Formula
C8H16N2O3
Molecular Weight
188.20
L-Asparagine tert-butyl ester
IUPAC Name
tert-butyl (2S)-2,4-diamino-4-oxobutanoate
Synonyms
L-Asn-OtBu; asparagine tert-butyl ester; H-ASN-OBUT; tert-butyl L-asparaginate; H-Asn-OtBu; L-Asparagine tert-butyl ester
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.113±0.06 g/cm3
Boiling Point
340.2±32.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C8H16N2O3/c1-8(2,3)13-7(12)5(9)4-6(10)11/h5H,4,9H2,1-3H3,(H2,10,11)/t5-/m0/s1
InChI Key
VLLGKVRQXXHELH-YFKPBYRVSA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CC(=O)N)N

L-Asparagine tert-butyl ester is a derivative of the amino acid asparagine, and it finds numerous applications in research and industrial settings. Here are some key applications of L-Asparagine tert-butyl ester:

Peptide Synthesis: L-Asparagine tert-butyl ester is widely used in the synthesis of peptides and proteins. Its protected functional group allows for selective reactions, aiding in the stepwise assembly of peptide sequences. This compound is instrumental in creating complex peptides for pharmaceutical research and therapeutic development.

Drug Delivery Systems: In pharmaceutical science, L-Asparagine tert-butyl ester can be used as a building block for creating prodrugs, which are inactive compounds that convert into active drugs in the body. By modifying drug molecules with L-Asparagine tert-butyl ester, researchers can improve drug stability, solubility, and bioavailability. This strategy is particularly useful for enhancing the efficacy of chemotherapy agents and other therapeutic compounds.

Biochemical Research: L-Asparagine tert-butyl ester is utilized in various biochemical studies to investigate enzyme-substrate interactions and protein folding mechanisms. Its unique structure allows for the probing of specific biochemical pathways and reactions. This application aids in understanding fundamental biological processes and developing novel biochemical assays.

Materials Science: L-Asparagine tert-butyl ester can be employed in the development of new materials, such as polymers and hydrogels. Its incorporation into polymer matrices can improve material properties such as biocompatibility and mechanical strength. These materials have potential applications in biomedical devices, tissue engineering, and drug delivery systems.

1.Preparation of N-acetyl, tert-butyl amide derivatives of the 20 natural amino acids.
Ekkati AR1, Campanali AA, Abouelatta AI, Shamoun M, Kalapugama S, Kelley M, Kodanko JJ. Amino Acids. 2010 Mar;38(3):747-51. doi: 10.1007/s00726-009-0279-y. Epub 2009 Mar 31.
N-Acetyl-AA(amino acid)-NHtBu derivatives of all 20 naturally occurring amino acids have been synthesized. Syntheses were performed via solution-phase methodology with yields that allow for access to gram quantities of substrates, in most cases. Syntheses include the coupling of a hindered amine, tert-butylamine, with each amino acid, either directly or in two steps using an activated ester isolated as an intermediate. The introduction of protecting groups was necessary in some cases. The development of synthetic sequences to access challenging substrates, such as the one derived from asparagine, are discussed.
2.Potential inhibitors of L-asparagine biosynthesis. 5. Electrophilic amide analogues of (S)-2,3-diaminopropionic acid.
Mokotoff M, Logue LW. J Med Chem. 1981 May;24(5):554-9.
Three electrophilic amide analogues of (S)-2,3-diaminopropionic acid (1, DAP) have been prepared as potential inhibitors of L-asparagine synthetase (ASase, from Novikoff hepatoma, EC 6.3.5.4). DAP was selectively blocked by the carbobenzoxy (Cbz) group to give 3-N-Cbz-DAP (2a). Esterification of 2a with isobutylene afforded tert-butyl 3-N-carbobenzoxy-(S)-2,3-diaminopropionate (3a), which was then blocked at the 2 position with the tert-butoxycarbonyl (Boc) group to give tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-[(carbobenzoxy)amino]propionate (4). Selective cleavage of the Cbz group by H2/Pd gave the key intermediate tert-butyl 2-N-(tert-butoxycarbonyl)-(S)-2,3-diaminopropionate (5), which was acylated, via the N-hydroxysuccinimide esters, with bromoacetic acid, dichloroacetic acid, and fumaric acid monoethyl ester to give tert-butyl 2-[(S)-(tert-butoxycarbonyl)-amino]-3-(2-bromoacetamido)propionate (6a), tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-(2,2-dichloroacetamido)propionate (6b), and tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-(ethoxycarbonyl)acrylamido]-propionate (6c), respectively.
3.Potential inhibitors of L-asparagine biosynthesis. 4. Substituted sulfonamide and sulfonylhydrazide analogues of L-asparagine.
Brynes S, Burckart GJ, Mokotoff M. J Med Chem. 1978 Jan;21(1):45-9.
Several N-substituted sulfonamides and N'-substituted sulfonylhydrazides have been prepared as sulfur analogues of L-asparagine with the potential of acting as inhibitors of L-asparagine synthetase (ASase, from Novikoff hepatoma). L-Cysteine was converted in known steps to N-carboxy-3-(sulfonylchloro)-L-alanine dibenzyl ester (1). Condensation of 1 with O-benzylhydroxylamine, p-(fluorosulfonyl)benzylamine, or monoethyl fumarylhydrazide (9), followed by deblocking with HF, gave 3-(hydroxysulfamoyl)-L-alanine (3a), 3-[p-(fluorosulfonylbenzyl)]sulfamoyl-L-alanine (3c), and 3-sulfo-L-alanine S-[2-[(E)-3-(ethoxycarbonyl)acryloyl]hydrazide] (3e), respectively. Similarly, 1 with 2-chloroethylamine and deblocking with H2-Pd gave 3-[(2-chloroethyl)sulfamoyl]-L-alanine (3b). tert-Butyl carbazate was allowed to react with 1 and the tert-butyl group was removed with HCl. The resulting sulfonylhydrazide 7 was condensed with p-(fluorosulfonyl)benzoyl chloride and then deblocked with HF to give 3-sulfo-L-alanine S-[2-[P-(fluorosulfonyl)benzoyl]hydrazide] (3d).
4.Synthesis of glycopeptides and neoglycoproteins containing the fucosylated linkage region of N-glycoproteins.
Unverzagt C1, Kunz H. Bioorg Med Chem. 1994 Nov;2(11):1189-201.
N-Glycoproteins fucosylated in the core region occur in tumor membranes and virus envelopes. Partial structures of such N-glycoproteins containing fucosylated chitobiosyl asparagine conjugates were synthesized using the allyloxycarbonyl (Aloc) and the tert-butyl ester protecting groups in the peptide portion. As the alpha-fucosidic bond of the conjugates revealed to be very sensitive to acids when carrying ether-type protecting groups, a method for exchanging the protecting groups of the fucose portion of saccharides was developed. Conjugates containing O-acetyl protected fucose proved to be stable against acids used in glycopeptide syntheses. These methods were applied in the synthesis of a fucosyl chitobiose hexapeptide with the partial sequence of a leukemia virus envelope glycoprotein. The glycopeptide was coupled to bovine serum albumin yielding a neoglycoprotein which contains a glycoconjugate of exactly specified structure.
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