Z-dehydroalanine methyl ester
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Z-dehydroalanine methyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-005756
CAS number
21149-17-7
Molecular Formula
C12H13NO4
Molecular Weight
235.24
Z-dehydroalanine methyl ester
IUPAC Name
methyl 2-(phenylmethoxycarbonylamino)prop-2-enoate
Synonyms
Z-Dehydro-Ala-OMe; N-Cbz-Dehydroalanine methyl ester; Z-Dha-OMe
Appearance
White solid
Purity
≥ 99% (HPLC)
Storage
Store at 2-8°C
InChI
InChI=1S/C12H13NO4/c1-9(11(14)16-2)13-12(15)17-8-10-6-4-3-5-7-10/h3-7H,1,8H2,2H3,(H,13,15)
InChI Key
STFUIEDYPRMRNN-UHFFFAOYSA-N
Canonical SMILES
COC(=O)C(=C)NC(=O)OCC1=CC=CC=C1

Z-dehydroalanine methyl ester, a versatile molecule with diverse applications in biochemistry and pharmacology, finds utility in various fields. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Frequently utilized in the chemical synthesis of peptides, Z-dehydroalanine methyl ester serves as a crucial component due to its unique structure. Acting as a precursor or intermediate in the creation of cyclic and modified peptides, this molecule plays a pivotal role in crafting peptides with specific biological activities and therapeutic potentials enriching the landscape of peptide synthesis with its varied applications.

Antimicrobial Research: Embraced in antimicrobial research endeavors, Z-dehydroalanine methyl ester is instrumental in the development of novel antimicrobial agents. By integrating this compound into peptide sequences, researchers can amplify the antimicrobial properties of these peptides offering a potent strategy against antibiotic-resistant bacterial strains and contributing to the continual evolution of antimicrobial research with innovative approaches.

Structural Biology: In the realm of structural biology, Z-dehydroalanine methyl ester emerges as a valuable tool particularly in the exploration of protein interactions and folding processes. Through the strategic introduction of this compound into polypeptide chains, researchers can introduce specific cross-links or modifications shedding light on protein structure and dynamics. This deepens our understanding of protein function and stability unravelling the intricate machinery that governs biological processes.

Enzyme Mechanism Studies: Serving as a valuable probe in enzyme mechanism studies, Z-dehydroalanine methyl ester enables the investigation of enzyme-substrate interactions and catalytic mechanisms. Leveraging its unique chemical reactivity, this compound forms covalent adducts with enzyme active sites facilitating in-depth exploration of enzyme function. This intricate understanding aids in the development of enzyme inhibitors for therapeutic applications illuminating new avenues for targeted drug discovery in the realm of enzyme mechanisms.

1. Characterization of grapevine fungal canker pathogens Fatty Acid Methyl Ester (FAME) profiles
Christopher M Wallis, Daniel P Lawrence, Renaud Travadon, Kendra Baumgartner Mycologia. 2022 Jan-Feb;114(1):203-213. doi: 10.1080/00275514.2021.1983396. Epub 2021 Dec 10.
Fatty acid methyl ester (FAME) analyses can be useful for distinguishing microbial species. This study conducted FAME analyses on 14 fungal species known to cause grapevine trunk diseases. FAME profiles were dominated by oleic acid, albeit profiles were characteristic enough to separate species. Discriminant analyses suggested that palmitoleic acid/sapienic acid, pentadecylic acid, and an unsaturated 17-carbon fatty acid (17:1ω8 c)could explain 79.8% of the variance in the profiles among species in the first three discriminant functions. FAME profile libraries were created for use in a commercialized software, which was able to accurately identify isolates to the species level, with a low rate (9.4%) of samples to be reassessed. Dendrograms created using neighbor-joining cluster analyses with data from FAME profiles were compared with those using internal transcribed spacer (ITS) region sequences. This revealed that FAME profiles, albeit useful for tentative species identification, should not be used for determining phylogenetic relationships because the dendrograms were significantly unconcordant. Regardless, these results demonstrated the potential of FAME analyses in quickly and initially identifying closely related fungal species or confirming conclusions from other species identification techniques that would require independent validation.
2. 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.
3. Binding of indomethacin methyl ester to cyclooxygenase-2. A computational study
Menyhárt-Botond Sárosi J Mol Model. 2018 Jun 5;24(7):150. doi: 10.1007/s00894-018-3686-8.
Inhibitors selective towards the second isoform of prostaglandin synthase (cyclooxygenase, COX-2) are promising nonsteroidal anti-inflammatory drugs and antitumor medications. Methylation of the carboxylate group in the relatively nonselective COX inhibitor indomethacin confers significant COX-2 selectivity. Several other modifications converting indomethacin into a COX-2 selective inhibitor have been reported. Earlier experimental and computational studies on neutral indomethacin derivatives suggest that the methyl ester derivative likely binds to COX-2 with a similar binding mode as that observed for the parent indomethacin. However, docking studies followed by molecular dynamics simulations revealed two possible binding modes in COX-2 for indomethacin methyl ester, which differs from the experimental binding mode found for indomethacin. Both alternative binding modes might explain the observed COX-2 selectivity of indomethacin methyl ester. Graphical abstract Binding of indomethacin methyl ester to cyclooxygenase-2.
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