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L-Aspartic acid α-tert-butyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

β−Amino Acids

Catalog number

BAT-004229

CAS number

4125-93-3

Molecular Formula

C8H15NO4

Molecular Weight

189.20

IUPAC Name

(3S)-3-amino-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid

Synonyms

L-Asp-OtBu; Asparaginsaeure; L-Lysine aspartate; Lysine aspartate; L-Lysine L-aspartate; L-tert-butyl aspartate

Appearance

White powder

Purity

≥ 98% (HPLC)

Density

1.162±0.06 g/cm3

Melting Point

180-181 °C

Boiling Point

297.8±30.0 °C

Storage

Store at 2-8 °C

InChI

InChI=1S/C8H15NO4/c1-8(2,3)13-7(12)5(9)4-6(10)11/h5H,4,9H2,1-3H3,(H,10,11)/t5-/m0/s1

InChI Key

PUWCNJZIFKBDJQ-YFKPBYRVSA-N

Canonical SMILES

CC(C)(C)OC(=O)C(CC(=O)O)N

L-Aspartic acid α-tert-butyl ester is a versatile compound with applications in various fields of bioscience and industry. Here are some key applications of L-Aspartic acid α-tert-butyl ester:

Peptide Synthesis: L-Aspartic acid α-tert-butyl ester is frequently used in the synthesis of peptides and proteins. It serves as a protecting group for the aspartic acid side chain, preventing unwanted side reactions during peptide chain assembly. This allows for the production of high-purity peptides, essential for pharmaceutical and biochemical research.

Pharmaceutical Intermediates: In the pharmaceutical industry, L-Aspartic acid α-tert-butyl ester is utilized as an intermediate in the synthesis of various active pharmaceutical ingredients (APIs). Its unique chemical properties facilitate the formation of complex molecular structures. This is critical for developing new drugs with enhanced efficacy and safety profiles.

Catalysis: L-Aspartic acid α-tert-butyl ester can be used as a chiral auxiliary in asymmetric synthesis reactions. By facilitating the creation of chiral centers, it aids in the production of optically active compounds. This application is vital for the development of enantiomerically pure pharmaceuticals and agrochemicals.

Biochemical Research: Researchers use L-Aspartic acid α-tert-butyl ester in studies related to enzyme mechanisms and protein folding. Its incorporation into experimental setups can help elucidate the functional roles of aspartic acid residues in proteins. This knowledge is crucial for understanding protein structure-function relationships and for designing enzyme inhibitors and activators.

2. An Olefination Entry for the Synthesis of Enantiopure alpha,omega-Diaminodicarboxylates and Azabicyclo[X.Y.0]alkane Amino Acids

Francis Gosselin, William D. Lubell J Org Chem. 1998 Oct 16;63(21):7463-7471. doi: 10.1021/jo9814602.

A new approach for synthesizing alpha,omega-diaminodicarboxylates of various chain lengths has opened the way for making a series of azabicyclo[X.Y.0]alkane amino acids of different ring sizes. beta-Keto phosphonates 21-23 were synthesized in 71-90% yield by the addition of the lithium anion of dimethyl methyl phosphonate to the omega-methyl ester of alpha-tert-butyl N-(PhF)aspartate 3, glutamate 9, and aminoadipate 12 (PhF = 9-phenylfluoren-9-yl). alpha,omega-Diaminodicarboxylates 24-26 of nine to eleven carbon chain lengths were prepared in 78-87% yield from the Horner-Wadsworth-Emmons olefination of alpha-tert-butyl N-(PhF)aspartate beta-aldehyde (5) with aminodicarboxylate-derived beta-keto phosphonates 21-23. The power of this approach for making azabicyclo[X.Y.0]alkane amino acid was then illustrated by the first synthesis of enantiopure indolizidin-9-one amino acid 2 in nine steps and >25% overall yield from inexpensive aspartic acid as chiral educt. Hydrogenation of (2S,8S)-di-tert-butyl 4-oxo-2,8-bis[N-(PhF)amino]non-4-enedioate (24) in 9:1 EtOH:AcOH furnished a 9:1 diastereomeric mixture of 6-alkylpipecolate 28 that was subsequently transformed into azabicyclo[4.3.0]alkane amino acid 2 via lactam cyclization and protecting group manipulations. Because alpha,omega-diaminodicarboxylates 25 and 26 may be similarly converted to heterocycles of larger ring sizes and because alkylation of similar ketones can be used to attach side-chains at different points on the heterocycle, this olefination strategy greatly expands our methodology for synthesizing azabicyclo[X.Y.0]alkane amino acids for the exploration of conformation-activity relationships of various biologically active peptides.