L-Aspartic acid β-tert-butyl ester
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L-Aspartic acid β-tert-butyl ester

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L-Aspartic acid 4-tert-butyl ester is a protected form of L-Aspartic acid. L-Aspartic acid is a non-essential amino acid that is used to biosynthesize other amino acids within the human body. L-Aspartic acid also increases membrane conductance of mammalian neurons by voltage-dependent means, causing depolarization and nerve impulses that travel to key areas of the central nervous system.

Category
L-Amino Acids
Catalog number
BAT-004122
CAS number
3057-74-7
Molecular Formula
C8H15NO4
Molecular Weight
189.20
L-Aspartic acid β-tert-butyl ester
IUPAC Name
(2S)-2-amino-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
Synonyms
L-Aspartic acid β-tert-butyl ester; L-aspartic acid 4-tert-butyl ester; (2S)-2-amino-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
Appearance
White powder
Purity
≥ 98% (Assay)
Density
1.162±0.06 g/cm3
Melting Point
220 °C (dec.)
Boiling Point
318.7±37.0 °C
Storage
Store at RT
InChI
InChI=1S/C8H15NO4/c1-8(2,3)13-6(10)4-5(9)7(11)12/h5H,4,9H2,1-3H3,(H,11,12)/t5-/m0/s1
InChI Key
MXWMFBYWXMXRPD-YFKPBYRVSA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)O)N

L-Aspartic acid β-tert-butyl ester, a derivative of L-aspartic acid, is widely used in various scientific and industrial applications. Here are some key applications of L-Aspartic acid β-tert-butyl ester:

Peptide Synthesis: L-Aspartic acid β-tert-butyl ester is commonly used as a building block in the synthesis of peptides and proteins. The tert-butyl ester group serves as a protecting group during the peptide assembly process, preventing unwanted reactions. This compound facilitates the creation of more complex peptide sequences by ensuring specificity and stability.

Pharmaceutical Development: In the pharmaceutical industry, L-Aspartic acid β-tert-butyl ester is utilized in the design and development of new drugs. Its chemical properties allow for its incorporation into drug molecules to enhance their stability and bioavailability. Researchers use it to explore new therapeutic compounds and improve drug formulations.

Biochemical Research: L-Aspartic acid β-tert-butyl ester is employed in biochemical studies to investigate enzyme-substrate interactions and metabolic pathways. Its structure makes it a valuable tool for probing the activity of aspartate-specific enzymes. This application helps in understanding enzyme mechanisms and facilitating the development of enzyme inhibitors.

Production of Specialty Chemicals: This ester derivative is also used in the production of specialty chemicals and intermediates in various industrial processes. Its reactivity and stability make it a valuable component in chemical manufacturing. Companies use it to produce high-purity chemicals for research and industrial applications.

1.Synthesis of the C-terminal half of thymosin alpha 1 by the polymeric reagent method.
Mokotoff M, Patchornik A. Int J Pept Protein Res. 1983 Feb;21(2):145-54.
In this report we further show the utility and efficiency of polymer-bound 1-hydroxybenzotriazole (PHBT) as an almost ideal support for the polymeric reagent method of peptide synthesis. This was demonstrated by the synthesis of thymosin alpha 1 (15-28), in which two suitably blocked segments, Boc-Asp (OtBu)-Leu-Lys (2Cz)-Glu (OBzl)-Lys (2Cz)-Lys (2Cz)-OH (3) and Boc-Glu (OBzl)-Val-Val-Glu (OBzl)-Glu (OBzl)-Ala-Glu (OBzl)-Asn-OBzl (2), were prepared entirely by utilizing PHBT activation for each coupling step. After appropriate deblocking of 2, segments 2 and 3 were coupled by the DCC-HOBT method, followed by complete deblocking and ion-exchange chromatographic purification, affording the C-terminal half of thymosin alpha 1, H-Asp-Leu-Lys-Glu-Lys-Lys-Glu-Val-Val-Glu-Glu-Ala-Glu-Asn-OH (1).
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