N-Benzyl-N-methyl-L-isoleucine
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N-Benzyl-N-methyl-L-isoleucine

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Category
L-Amino Acids
Catalog number
BAT-004063
CAS number
4125-97-7
Molecular Formula
C14H21NO2
Molecular Weight
235.33
N-Benzyl-N-methyl-L-isoleucine
IUPAC Name
(2S,3S)-2-[benzyl(methyl)amino]-3-methylpentanoic acid
Synonyms
Bzl-N-Me-L-Ile-OH; Z-N-ME-ISOLEUCINE; Z-L-MEILE-OH; NALPHA-Benzyloxycarbonyl-N-methyl-L-isoleucine; Z-N-ME-ILE-OH; N-Benzyl-N-methyl-isoleucin
Appearance
White powder
Purity
≥ 98% (Assay)
Density
1.145 g/cm3
Melting Point
140-146 °C
Boiling Point
419.4 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H21NO2/c1-4-11(2)13(14(16)17)15(3)10-12-8-6-5-7-9-12/h5-9,11,13H,4,10H2,1-3H3,(H,16,17)/t11-,13-/m0/s1
InChI Key
UMCNRCSUWIPPOC-AAEUAGOBSA-N
Canonical SMILES
CCC(C)C(C(=O)O)N(C)CC1=CC=CC=C1
1. Synthesis of a docosapeptide comprising the hydrophobic membrane spanning region of glycophorin A
R E Galardy, Z P Kortylewicz Int J Pept Protein Res. 1985 Jul;26(1):33-48. doi: 10.1111/j.1399-3011.1985.tb03175.x.
The docosapeptide which constitutes the membrane spanning region (amino acid residues 73-94) of the human red blood cell protein glycophorin A has been synthesized. This may be the first example of the synthesis of the entire membrane embedded domain of a membrane spanning protein. Three fully protected fragments were prepared by stepwise elongation using dicyclohexylcarbodiimide and p-nitrophenyl ester activation of N alpha-tert.-butyloxycarbonyl amino acids. The three fragments represent amino acid residues 73-79, 80-86, and 87-94 in the sequence of glycophorin A and contain a large proportion of valine, leucine, and isoleucine residues but contain no amino acids with ionizable side chain functional groups. The three fragments were condensed using both the azide method and the dicyclohexylcarbodiimide method to give fully protected docosapeptide. Benzyl groups protecting the side chains of the docosapeptide were removed by prolonged hydrogenolysis to give the desired product N alpha-tert.-butyloxycarbonyldocosapeptide ethyl ester. High resolution proton n.m.r. spectra of the protected fragments in 100% deuterochloroform showed all resonances to be broadened with the amide resonances broadened beyond recognition. In perdeuterodimethylsulfoxide all resonances were relatively sharp with all amide resonances visible and showing coupling constants of 7-8 Hz. Solvent titration of the proton spectra of two of the fragments from 100% perdeuterodimethylsulfoxide to 100% deuterochloroform demonstrated a transition to the broadened spectrum, accompanied by a decrease in the coupling constant of the amide protons (JNH-CH alpha) suggesting solvent dependent onset of intramolecular secondary structure, possibly accompanied by aggregation. A proton n.m.r. spectrum of the docosapeptide in perdeuterodimethylsulfoxide shows a few resolved amide resonances with coupling constants of 7-9 Hz. Solvent titration with perdeuterochloroform again suggests a transition to a rigid intramolecular secondary structure.
2. Comparative analysis of sugar, acid, and volatile compounds in CPPU-treated and honeybee-pollinated melon fruits during different developmental stages
Haiwen Chen, Jintao Cheng, Yuan Huang, Qiusheng Kong, Zhilong Bie Food Chem. 2023 Feb 1;401:134072. doi: 10.1016/j.foodchem.2022.134072. Epub 2022 Sep 1.
Plant growth regulator N-(2-chloro-4-pyridyl)-N'-phenylurea (CPPU) is widely used in fruit production. However, the mechanism in which CPPU affects melon fruit quality, especially aroma compound, remains unclear. Here, gas chromatography-mass spectrometry was performed to detect the sugar, citric acid, and aroma content in CPPU-treated and pollinated melon fruit. Results showed that the application of CPPU decreased the sugar and aroma content in melon fruit. The relative content of several important esters, including isobutyl acetate, ethyl acetate, 2-methylbutyl acetate, methyl acetate, benzyl acetate, and phenethyl acetate, in CPPU-treated fruits was significantly lower than that in honeybee-pollinated fruits. The content of many amino acids (isoleucine, leucine, valine, methionine, and l-phenylalanine), which could be metabolized into aroma compounds, in CPPU-treated fruits was significantly higher than that in honeybee-pollinated fruits. In conclusion, CPPU application interferes with amino-acid metabolism and affects the production of aromatic esters in melon fruit.
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