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Application Area

L-Aspartic acid β-cyclohexyl ester

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

Category

L-Amino Acids

Catalog number

BAT-004119

CAS number

112259-66-2

Molecular Formula

C10H17NO4

Molecular Weight

215.30

IUPAC Name

(2S)-2-amino-4-cyclohexyloxy-4-oxobutanoic acid

Synonyms

L-Asp(OcHex)-OH; ASPARTIC ACID-4-CYCLOHEXYL ESTER; L-Aspartic acid B-cyclohexyl ester

Appearance

White to off-white powder

Purity

≥ 98%

Density

1.20±0.1 g/cm3

Boiling Point

386.2±37.0 °C

Storage

Store at RT

InChI

InChI=1S/C10H17NO4/c11-8(10(13)14)6-9(12)15-7-4-2-1-3-5-7/h7-8H,1-6,11H2,(H,13,14)/t8-/m0/s1

InChI Key

IJAPBBOAGRLKMH-QMMMGPOBSA-N

Canonical SMILES

C1CCC(CC1)OC(=O)CC(C(=O)O)N

L-Aspartic acid β-cyclohexyl ester is a versatile chemical compound with various applications in bioscience and industry. Here are some key applications of L-Aspartic acid β-cyclohexyl ester:

Pharmaceutical Synthesis: L-Aspartic acid β-cyclohexyl ester is used as an intermediate in the synthesis of pharmaceuticals. It can be incorporated into complex molecular structures, aiding in the development of drugs for various therapeutic purposes. Its unique ester group offers opportunities for further chemical modifications to enhance drug properties.

Peptide Synthesis: This ester derivative is valuable in the synthesis of peptides and proteins. By protecting the aspartic acid residue during peptide assembly, it helps ensure the correct sequence and structure of the final product. The β-cyclohexyl group can be selectively removed at a later stage, facilitating efficient peptide elongation and purification.

Chiral Building Block: As a chiral molecule, L-Aspartic acid β-cyclohexyl ester serves as a precursor for the synthesis of enantiomerically pure compounds. Its stereochemistry is crucial for producing compounds with specific biological activities. This application is particularly important in the agrochemical and pharmaceutical industries, where chirality can influence the efficacy and safety of active ingredients.

Biodegradable Polymers: L-Aspartic acid β-cyclohexyl ester can be utilized in the production of biodegradable polymers. These polymers are employed in medical devices, tissue engineering, and environmentally-friendly packaging materials. The ester linkage in the polymer backbone enhances biodegradability while maintaining structural integrity.

1. Design of protecting groups for the beta-carboxylic group of aspartic acid that minimize base-catalyzed aspartimide formation

A Karlström, A Undén Int J Pept Protein Res. 1996 Oct;48(4):305-11. doi: 10.1111/j.1399-3011.1996.tb00846.x.

With the objectives of developing new protecting groups for the beta-carboxyl group of aspartic acid that are resistant to base-catalyzed aspartimide formation and of evaluating the importance of sterical factors in the design of such protecting groups, four new alkyl ester derivatives of aspartic acid were synthesized. The beta-3-pentyl, beta-4-heptyl, beta-2,6-dimethyl-4-heptyl and the recently described beta-2,4-dimethyl-3-pentyl esters of Boc-aspartic acid were incorporated into model peptides, and the resin-bound protected peptides were treated with 20% piperidine for 10 h. The levels of aspartimide-related side products were compared with the previously reported beta-cyclohexyl, beta-menthyl and beta-2-adamantyl esters of aspartic acid. The results show that bulky, acyclic, aliphatic protecting groups (in particular the 2,4-dimethyl-3-pentyl ester) are significantly more resistant to base-catalyzed aspartimide formation than comparably rigid cyclic alkyl esters that under the same reaction conditions form several-fold more aspartimide-related side products. Using elevated temperatures to overcome difficult couplings leads to the formation of significant amounts of aspartimide when aspartic acid is protected with the cyclohexyl group, but the 2,4-dimethyl-3-pentyl protecting group offers excellent protection under these conditions. The use of the 2,4-dimethyl-3-pentyl protecting group will allow the use of orthogonally removable base-labile protecting groups in Boc chemistry and suggests a design of protecting groups for other nucleophile-sensitive trifunctional amino acids in both Boc and Fmoc chemistry.

2. The synthesis of alternative diketopiperazines as potential RGD mimetics

Nikolett Mihala, Antal Csámpai, Janez Ilas, Danijel Kikelj, Robert Kiss, Helga Süli-Vargha J Pept Sci. 2006 Oct;12(10):663-9. doi: 10.1002/psc.776.

Alternative RGD mimetics-with the exception of glycine-c(Arg-Asp) 1, c(Arg-Glu) 2 and c[Arg-Asp(Phe-OH)] 3 were synthesized. The DKPs were prepared on solid phase with orthogonal protection allowing further derivatization in solution. During solution phase cyclization in NH(3)/methanol, the side chain benzyl ester group of H-Arg(Tos)-Asp(OBzl)-OMe and H-Arg(Tos)-Glu(OBzl)-OMe suffer transesterification, while beta-t-butyl or beta-cyclohexyl esters are stable under the same conditions. In spite of the simple structure, all compounds bind selectively to the alpha(v)beta(3) integrin receptor, 3 showing the highest affinity with an IC(50) value of 0.74 microM value. On the other hand only 3 binds with measurable activity to the alpha(IIb)beta(3) receptor (IC(50) 159 microM). The binding affinities seem to be in accordance with the distances between the arginine guanidino and the aspartic acid carboxyl group in extended conformation determined by semiempirical geometry optimization.