Z-L-aspartic acid β-cyclohexyl ester
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Z-L-aspartic acid β-cyclohexyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-003330
CAS number
211797-21-6
Molecular Formula
C18H23NO6
Molecular Weight
349.35
Z-L-aspartic acid β-cyclohexyl ester
IUPAC Name
(2S)-4-cyclohexyloxy-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid
Synonyms
Z-L-Asp(OcHex)-OH; (S)-2-(((Benzyloxy)Carbonyl)Amino)-4-(Cyclohexyloxy)-4-Oxobutanoic Acid
Appearance
White to off-white solid
Purity
≥ 99% (HPLC)
Melting Point
72-76 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C18H23NO6/c20-16(25-14-9-5-2-6-10-14)11-15(17(21)22)19-18(23)24-12-13-7-3-1-4-8-13/h1,3-4,7-8,14-15H,2,5-6,9-12H2,(H,19,23)(H,21,22)/t15-/m0/s1
InChI Key
FRMQHBWAORFCPR-HNNXBMFYSA-N
Canonical SMILES
C1CCC(CC1)OC(=O)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2

Z-L-aspartic acid β-cyclohexyl ester, a specialized compound with diverse applications in biochemical research and pharmaceutical development, is a key player in several critical areas. Here are four key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental component of peptide synthesis, Z-L-aspartic acid β-cyclohexyl ester acts as a shielded amino acid, safeguarding against undesired reactions in the coupling process. The cyclohexyl ester group plays a pivotal role in facilitating the precise and efficient assembly of peptide chains, crucial for the creation of innovative therapeutic peptides and the exploration of protein interactions.

Drug Development: Harnessing its distinctive composition, this compound emerges as a foundational element in the construction of novel drug molecules. By integrating Z-L-aspartic acid β-cyclohexyl ester into drug candidates, researchers elevate the stability and bioavailability of these compounds. Its participation in structure-activity relationship studies contributes to refining drug efficacy and mitigating potential adverse effects, steering drug development towards enhanced outcomes.

Enzyme Inhibition Studies: Unveiling its potential in the domain of enzyme inhibition, Z-L-aspartic acid β-cyclohexyl ester aids in the design of potent enzyme inhibitors. By mirroring the structure of natural substrates, it illuminates the intricate interactions between enzymes and substrates. This comprehension serves as a linchpin in crafting inhibitors capable of modulating enzymatic behaviors, a critical pursuit across therapeutic domains like cancer and metabolic disorders.

Chiral Synthesis: Within the realm of organic chemistry, Z-L-aspartic acid β-cyclohexyl ester assumes a central role in chiral synthesis, enabling the production of chiral intermediates. Its enantiomerically pure form stands as a cornerstone in the creation of molecules with precise stereochemical arrangements. This facet proves particularly vital in pharmaceutical synthesis, where the chirality of a drug exerts a profound influence on its effectiveness and safety, underscoring the significance of Z-L-aspartic acid β-cyclohexyl ester in advancing pharmaceutical science.

1.Influence of reaction conditions on syntheses of sweetener precursors catalyzed by thermolysin in tert-amyl alcohol.
Xing GW1, Tian GL, Ye YH. J Pept Res. 1998 Oct;52(4):300-4.
The activity of enzymes to form a peptide bond in organic solvent was greatly influenced by observed pH and water content. The precursors of two sweeteners, P-Asp-Xaa-OR (P=Z or For, Xaa-OR=Phe-OMe or Ala-OcHex), were synthesized by enzyme, and the reaction conditions were studied systematically. Z-Asp-OH was coupled with H-Phe-OMe or H-Ala-OcHex by thermolysin in tert-amyl alcohol. The best coupling results were obtained when the optimized observed pH was 8 or 9, and the water content was about 6% (V/V). The protecting group Z is better than For under the reaction conditions and H-Phe-OMe is a better nucleophile than H-Ala-OcHex. The expected optically pure peptides were obtained when the racemic amino acids were used as amino components in the starting materials. The physical constants of P-Asp-Xaa-OR synthesized by thermolysin are identical with those of peptides synthesized by chemical method.
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