53363-89-6

Usage

Uses

Used in Pharmaceutical Industry:
Boc-N-methyl-L-leucine is used as an amino acid building block for peptide synthesis, which is crucial in the fast and reliable synthesis of peptides. This is particularly important due to the growing peptide drug market, where the development of therapeutic peptide compounds relies on the availability and properties of amino acid building blocks like Boc-N-methyl-L-leucine.
Used in Research and Development:
Boc-N-methyl-L-leucine is used as a key component in the assay of biological activity of modified peptides. Its N-methylated structure allows for the study of the effects on proteolytic stability, membrane permeability, and peptide conformation, which are essential aspects in understanding the behavior and potential applications of these modified peptides in various research and development projects.

References

https://en.wikipedia.org/wiki/Tert-Butyloxycarbonyl_protecting_group http://pubs.acs.org/doi/abs/10.1021/cr030024z?src=recsys&journalCode=chreay

InChI:InChI=1/C12H23NO4/c1-8(2)7-9(10(14)15)13(6)11(16)17-12(3,4)5/h8-9H,7H2,1-6H3,(H,14,15)/t9-/m0/s1

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 61-90-5 L-leucine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 130994-88-6 methyl N-methyl-N-(tert-butoxycarbonyl)-L-leucinate 
• 172096-97-8 (4S)-N-(tert-butyloxycarbonyl)-4-isobutyl-1,3-oxazolidin-5-one 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 159392-24-2 N-BOC-MeLeu-Phe-OH benzyl ester 
• 153052-68-7 (2R)-1-(benzyloxy)-1-oxopropan-2-yl (2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoate 
• 153052-70-1 benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate 
• 172922-45-1 2-[(R)-1-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-2-(1-methyl-1H-indol-3-yl)-ethyl]-5-methyl-1H-imidazole-4-carboxylic acid benzyl ester 
• 248922-88-5 (S)-{1-[4,4-bis-(4-fluoro-phenyl)-butylcarbamoyl]-3-methyl-butyl}-methyl-carbamic acid tert-butyl ester 
• 188908-73-8 (S)-2-{(R)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-2-oxo-pyrrolidin-1-yl}-4-methyl-pentanoic acid benzyl ester 
• 188909-02-6 (S)-2-{(R)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyloxy]-2-oxo-piperidin-1-yl}-4-methyl-pentanoic acid benzyl ester 
• 863781-38-8 N-(tert-butoxycarbonyl)-N-methyl-L-leucyl-L-phenylalanine methyl ester 
• 248922-46-5 (S)-4-methyl-2-(methylamino)pentanoic acid [4,4-bis(4-fluorophenyl)butyl]amide 
• 217171-01-2 2-[(4-tert-butyl-benzyl)-methyl-amino]-4-methyl-pentanoic acid [2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-amide 
• 141205-31-4 microcolin A 

Relevant academic research and scientific papers

Preparation method of N-trimethyl silicon ethoxycarbonyl-N-methyl-L/D-leucine

The invention relates to a preparation method of N-(trimethylsilyl) ethoxycarbonyl group-N-methyl-L/D-leucine. The preparation method comprises the following steps: adding N-methyl-L/D-leucine hydrochloride, a trimethylsilylethoxycarbonyl protecting group reagent and alkali into a mixed solution of a polar solvent and water, and carrying out a reaction, so as to obtain the N-trimethylsilylethoxycarbonyl-N-methyl-L/D-leucine. According to the preparation method, the N-trimethyl silicon ethoxycarbonyl-N-methyl-L/D-leucine with high chiral purity, high chemical purity and high yield can be obtained, the chiral purity and the chemical purity can reach 99% or above, the yield can reach 60% or above, and the preparation method is simple in process, mild in condition and suitable for being applied to large-scale industrial production.

Elucidation of absolute configuration of ophiorrhiside a by comparison of ecd spectra with that of model chiral compound having a 1,2,3,4-tetrahydro-β-carbolin-3-one skeleton

A chiral 1,2,3,4-tetrahydro-β-carbolin-3-one having a substituent at C-1 was synthesized from L-leucine and used to elucidate the absolute configuration at C-3 of ophiorrhiside A, a monoterpenoid glucoindole alkaloid.

ENDOPARASITIC DEPSIPEPTIDES

The present invention provides cyclic depsipeptides of Formula (1), stereoisomers thereof, and veterinary acceptable salts thereof (1) wherein each of R1, R2, R3, R4, L1, and L2, are as defined herein. The present invention also contemplates compositions and methods of treatment as an endoparasiticide with a Formula (1) compound.

ENDOPARASITIC DEPSIPEPTIDES

The present invention provides cyclic depsipeptides of Formula (1), stereoisomers thereof, and veterinary acceptable salts thereof wherein each of R1, R2, R3, R4, L1, and L2 are as defined herein. The present invention also contemplates compositions, methods of treatment, and uses as a medicament to treat an animal for an endoparasitic infection with a Formula (1 ) compound.

Antineoplastic activity of linear leucine homodipeptides and their potential mechanisms of action

Galaxamide is a rare cyclic homopentapeptide composed of three leucines and two N-methyl leucines isolated from marine algae Galaxaura filamentosa. The strong antitumor activity of this compound makes it a promising candidate for tumor therapy. The synthesis of galaxamide, however, is a complex process, and it has poor water solubility. On the basis of its special chemical composition, we designed a series of linear leucine homopeptides. Among seven dipeptide derivatives, five compounds with terminal protection groups and methyl substitution of the hydrogen in the amido group showed remarkable inhibitory effects against various cancer cells. N-Tertbutyl-d-leucine-N-methyl-d-leucinebenzyl (A7), the only stereomer condensed by two d-leucines, showed the highest antineoplastic activity. A7-Treated cells showed cell cycle arrest and morphological changes typical of cells undergoing apoptosis. The population of Annexin-V positive/propidium iodide-negative cells also increased, indicating the induction of early apoptosis. A7 promoted the cleavage of caspase-9 and caspase-3, as well as increased intracellular Ca 2+ levels and decreased the mitochondrial membrane potential. Collectively, certain linear leucine dipeptides derived from cyclic pentapeptide are able to inhibit tumor cell proliferation through cell cycle arrest and apoptosis induction. The N-methyl group in the side chain and the d/l conformation of the amino-Acid residue are critical for their activity.

D-amino acid position influences the anticancer activity of galaxamide analogs: An apoptotic mechanism study

Galaxamide, an extract from Galaxaura filamentosa, is a cyclic pentapeptide containing five L-leucines. Due to the particular cyclic structure and the excellent anticancer activity, synthesis of Galaxamide and its analogs and their subsequent bio-applications have attracted great attention. In the present work, we synthesized six Galaxamide analogs by replacing one of the L-leucines with phenylalanine and varying the D-amino acid position. The anticancer effect of the synthesized Galaxamide analogs was tested against four in vitro human cancer cell lines, human hepatocellular cells (HepG2), human breast cancer cell (MCF-7), human breast adenocarcinoma cells (MDA-MB-435) and a human cervical carcinoma cell line (Hela). Results showed that Galaxamide analogs with differentD-amino acid positions displayed distinct anticancer potential. The Galaxamide analog containing D-amino acid at position 5 (Analog-6) presented the strongest anticancer activity. The mechanism study revealed that Analog-6 could cause the early apoptosis of HepG2 cells by inhibiting their growth in the sub-G1 stage of the cell cycle and induce the chromatin condensation and fragmentation, which can be seen as 68% of HepG2 cells inhibited in the sub-G1 stage. Moreover, a mitochondria-mediated pathway was found to be involved in the apoptotic process of Analog-6 on HepG2 cells.

Design, synthesis, and in vitro antiplasmodial activity of 4-aminoquinolines containing modified amino acid conjugates

Abstract: A new series of side chain-modified 4-aminoquinolines were synthesized and screened for in vitro antiplasmodial activity against both chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum. Among the series, compounds 30 and 31 showed significant inhibition of parasite growth against K1 strain of P. falciparum with IC50 values 0.28 and 0.31?μM, respectively, whereas compounds 34, 35, and 38 exhibited superior activity against K1 strain with IC50 values 0.18, 0.22, and 0.17?μM, respectively, as compared to 0.255?μM for chloroquine (CQ). All the compounds displayed good resistance factor between 1.54 and >34.48 as against 51.0 for CQ. All these analogues were found to form strong complex with hematin and inhibited the β-hematin formation in vitro, suggesting that this class of compounds act on a heme polymerization target. Overall results suggest that present series of compounds appear to be promising for further lead optimization to obtain compounds active against drug-resistant parasites. Graphical Abstract: [Figure not available: see fulltext.]

Total synthesis of proposed structure of coibamide A, a highly N- and O-methylated cytotoxic marine cyclodepsipeptide

Total synthesis of the originally proposed structure of coibamide A, a highly N- and O-methylated cytotoxic marine cyclodepsipeptide, has been accomplished by using a [(4+1)+3+3]-peptide fragment-coupling strategy and careful examination and optimization

DERIVATIVES OF DOLASTATIN 10 AND AURISTATINS

The present invention concerns a compound of following formula (I): where: - R1 is H or OH, - R2 is a (C1-C6)alkyl, COOH, COO-((C1-C6)alkyl) or thiazolyl group, - R3 is H or a (C1-C6)alkyl group, and - R4 is: ■ a straight-chain or branched, saturated or unsaturated hydrocarbon group having 1 to 8 carbon atoms substituted by one or more groups chosen from among OH and NR5R6, ■ -(CH2CH2X1)(CH2CH2X2)a2(CH2CH2X3)a3(CH2CH2X4)a4(CH2CH2X5)a5R7, ■ an aryl-(C1-C8)alkyl group substituted by one or more groups chosen from among OH and NR9R10 groups, or ■ a heterocycle-(C1-C8)alkyl group optionally substituted by one or more groups chosen from among (C1-C6)alkyl, OH and NR12R13 groups, or a pharmaceutically acceptable salt, hydrate or solvate thereof, and its uses in particular for the treatment of cancer, pharmaceutical compositions containing the same and the preparation methods thereof.

Selective peptide modifications via ruthenium-catalyzed allylic alkylations

Ruthenium-catalyzed allylic alkylations are an interesting alternative to palladium-catalyzed processes, since they can provide products which are not accessible under Pd-catalysis. Chiral terminal allylic substrates can be reacted with perfect stereo- and regioretention, and also (Z)-configured allylic substrates can be converted isomerization-free. This allows highly stereoselective modifications of peptides at glycine subunits. The configuration at the α-position of the new generated α-amino acid can be controlled by the chiral peptide chain, and at the β-position by using chiral allylic substrates.