Boc-β-cyclohexyl-L-alanine methyl ester
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Boc-β-cyclohexyl-L-alanine methyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-007188
CAS number
98105-41-0
Molecular Formula
C15H27NO4
Molecular Weight
285.38
Boc-β-cyclohexyl-L-alanine methyl ester
IUPAC Name
methyl (2S)-3-cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
Boc-β-cyclohexyl-L-alanine methyl ester; Boc-3-cyclohexyl-L-alanine methyl ester
Appearance
White solid
Purity
≥ 95% (HPLC)
Density
1.034 g/cm3
Melting Point
47-49 °C
Boiling Point
386.9°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C15H27NO4/c1-15(2,3)20-14(18)16-12(13(17)19-4)10-11-8-6-5-7-9-11/h11-12H,5-10H2,1-4H3,(H,16,18)/t12-/m0/s1
InChI Key
FALUXMVPGFKLAM-LBPRGKRZSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1CCCCC1)C(=O)OC

Boc-β-cyclohexyl-L-alanine methyl ester, a synthetic amino acid derivative, finds diverse applications in chemical and biotechnological research. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: A cornerstone in solid-phase peptide synthesis, Boc-β-cyclohexyl-L-alanine methyl ester acts as a vital building block imbuing peptides with structural rigidity and hydrophobicity thereby enhancing their stability and bioactivity. This derivative plays a crucial role in crafting novel peptide drugs and biomolecules tailored for therapeutic and diagnostic purposes showcasing its versatility in peptide design and synthesis.

Drug Development: At the forefront of drug discovery, Boc-β-cyclohexyl-L-alanine methyl ester emerges as a key player in the design and synthesis of small molecule inhibitors and peptide-based drugs. Through its integration into pharmacologically active compounds researchers can fine-tune drug-receptor interactions and enhance pharmacokinetic properties. This derivative serves as an invaluable asset in unraveling structure-activity relationships paving the way for the creation of more potent and selective therapeutic agents.

Proteomics Research: In the realm of proteomics, Boc-β-cyclohexyl-L-alanine methyl ester serves as a labeled amino acid for mass spectrometry analysis enabling the identification and quantification of peptides and proteins with precision. By furnishing a distinctive mass signature, this derivative plays a pivotal role in dissecting protein expression post-translational modifications and protein-protein interactions offering insights into the intricate world of proteomic dynamics.

Chemical Biology: A versatile instrument in chemical biology, Boc-β-cyclohexyl-L-alanine methyl ester facilitates the exploration of protein structure and function. Through its incorporation into proteins via site-specific mutagenesis, researchers can delve into the functions of specific residues in catalysis binding and folding unraveling the mysteries of protein mechanisms and unearthing novel biochemical pathways. This approach stands as a cornerstone in advancing our understanding of complex biological systems through detailed protein studies.

1. Acridinium Ester Chemiluminescence: Methyl Substitution on the Acridine Moiety
Manabu Nakazono, Shinkoh Nanbu, Takeyuki Akita, Kenji Hamase J Oleo Sci. 2021;70(11):1677-1684. doi: 10.5650/jos.ess21186.
Methyl groups were introduced on the acridine moiety in chemiluminescent acridinium esters that have electron-withdrawing groups (trifluoromethyl, cyano, nitro, ethoxycarbonyl) at the 4-position on the phenyl ester. The introduction of methyl groups at the 2-, 2,7-, and 2,3,6,7-positions on the acridine moiety shifted the optimal pH that gave relatively strong chemiluminescence intensity from neutral conditions to alkaline conditions. 4-(Ethoxycarbonyl)phenyl 2,3,6,7,10-pentamethyl-10λ4-acridine-9-carboxylate, trifluoromethanesulfonate salt showed long-lasting chemiluminescence under alkaline conditions. Acridinium esters to determine hydrogen peroxide concentration at pH 7-10 were newly developed.
2. O-Methylation of carboxylic acids with streptozotocin
Li-Yan Zeng, Yang Liu, Jiakun Han, Jinhong Chen, Shuwen Liu, Baomin Xi Org Biomol Chem. 2022 Jul 6;20(26):5230-5233. doi: 10.1039/d2ob00578f.
The clinically used DNA-alkylating drug streptozotocin (STZ) was investigated using a simple work-up as an O-methylating agent to transform various carboxylic acids, sulfonic acids and phosphorous acids into corresponding methyl esters, and did so with yields of up to 97% in 4 h at room temperature. Good substrate tolerance was observed, and benefited from the mild conditions and compatibility of the reaction with water.
3. Alginate ester: New moisture-scavenging excipients for direct compressible pharmaceutical tableting
Noelia M Sanchez-Ballester, Philippe Trens, Jean-Christophe Rossi, Ian Soulairol Carbohydr Polym. 2022 Dec 1;297:120063. doi: 10.1016/j.carbpol.2022.120063. Epub 2022 Aug 31.
The objective of this work is to evaluate methyl ester alginates and alginic acid (AA) as moisture-scavenging excipients for the formulation of aspirin tablets obtained by direct compression. The tablets were stored at accelerated conditions (40 °C/75 % RH) and assessed for changes in tensile strength, mass, thickness and disintegration time. While moisture caused a reduction in the hardness of MCC and AA tablets, hardness of the tablets made from methylated materials was virtually unaffected. The physical stability of alginate ester tablets was found to be related to their increased plastic deformation leading to extended interparticle contact with less impact on tablet porosity. Finally, the combination of higher moisture affinity and lower water dissociation exhibited by alginates esters resulted in tablets with the lowest aspirin degradation. These findings suggest that excipients with high water retention can act as moisture-scavengers without losing their functional properties and reducing the degradation of moisture-sensitive drugs.
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