N-α-Acetyl-L-isoleucine N-methylamide
Need Assistance?
  • US & Canada:
    +
  • UK: +

N-α-Acetyl-L-isoleucine N-methylamide

* 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-005936
CAS number
32483-16-2
Molecular Formula
C9H18N2O2
Molecular Weight
186.25
N-α-Acetyl-L-isoleucine N-methylamide
IUPAC Name
(2S,3S)-2-acetamido-N,3-dimethylpentanamide
Alternative CAS
120328-70-3
Synonyms
Ac-Ile-NHMe
Purity
99%
Density
0.981±0.06 g/cm3
Boiling Point
409.0±28.0 °C
Storage
Store at RT
InChI
InChI=1S/C9H18N2O2/c1-5-6(2)8(9(13)10-4)11-7(3)12/h6,8H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-,8-/m0/s1
InChI Key
VFPIEHZHPRLCOB-XPUUQOCRSA-N
Canonical SMILES
CCC(C)C(C(=O)NC)NC(=O)C
1. N-Methylamide-structured SB366791 derivatives with high TRPV1 antagonistic activity: toward PET radiotracers to visualize TRPV1
Tatsuya Kida, et al. RSC Med Chem. 2022 Sep 6;13(10):1197-1204. doi: 10.1039/d2md00158f. eCollection 2022 Oct 19.
Transient receptor potential cation channel subfamily V member 1 (TRPV1)-targeted compounds were synthesized by modifying the structure of SB366791, a pharmaceutically representative TRPV1 antagonist. To avoid amide-iminol tautomerization, structurally supported N-methylated amides (i.e., 3-alkoxy-substitued N-meythylamide derivatives of SB366791) were evaluated using a Ca2+ influx assay, in which cells expressed recombinant TRPV1 in the presence of 1.0 μM capsaicin. The antagonistic activities of N-(3-methoxyphenyl)-N-methyl-4-chlorocinnamamide (2) (RLC-TV1004) and N-{3-(3-fluoropropoxy)phenyl}-N-methyl-4-chlorocinnamamide (4) (RLC-TV1006) were found to be approximately three-fold higher (IC50: 1.3 μM and 1.1 μM, respectively) than that of SB366791 (IC50: 3.7 μM). These results will help reinvigorate the potential of SB366791 in medicinal chemistry applications. The 3-methoxy and 3-fluoroalkoxy substituents were used to obtain radioactive [11C]methoxy- or [18F]fluoroalkoxy-incorporated tracers for in vivo positron emission tomography (PET). Using the 11C- or 18F-labeled derivatives, explorative PET imaging trials were performed in rats.
2. Conformational preferences of N-acetyl-L-leucine-N'-methylamide. Gas-phase and solution calculations on the model dipeptide
Marcelo F Masman, Sandor Lovas, Richard F Murphy, Ricardo D Enriz, Ana M Rodríguez J Phys Chem A. 2007 Oct 25;111(42):10682-91. doi: 10.1021/jp0716886. Epub 2007 Sep 21.
A DFT study of N-acetyl-l-leucine-N'-methylamide conformers in the gas phase and in solution was carried out. The theoretical computational analysis revealed 43 different conformations at the B3LYP/6-31G(d) level of theory in the gas phase. In addition, the effects of three solvents (water, acetonitrile, and chloroform) were included in the calculations using the isodensity polarizable continuum model (IPCM) and the Poisson-Boltzmann self-consistent reaction field (PB-SCRF) method. The stability order of the different conformers in solution has been analyzed. The theoretical results were compared with some experimental data (X-ray, IR, and NMR).
3. Amide Spectral Fingerprints are Hydrogen Bonding-Mediated
Sara Gómez, Cettina Bottari, Franco Egidi, Tommaso Giovannini, Barbara Rossi, Chiara Cappelli J Phys Chem Lett. 2022 Jul 7;13(26):6200-6207. doi: 10.1021/acs.jpclett.2c01277. Epub 2022 Jun 30.
The origin of the peculiar amide spectral features of proteins in aqueous solution is investigated, by exploiting a combined theoretical and experimental approach to study UV Resonance Raman (RR) spectra of peptide molecular models, namely N-acetylglycine-N-methylamide (NAGMA) and N-acetylalanine-N-methylamide (NALMA). UVRR spectra are recorded by tuning Synchrotron Radiation at several excitation wavelengths and modeled by using a recently developed multiscale protocol based on a polarizable QM/MM approach. Thanks to the unparalleled agreement between theory and experiment, we demonstrate that specific hydrogen bond interactions, which dominate hydration dynamics around these solutes, play a crucial role in the selective enhancement of amide signals. These results further argue the capability of vibrational spectroscopy methods as valuable tools for refined structural analysis of peptides and proteins in aqueous solution.
Online Inquiry
Verification code
Inquiry Basket