53363-89-6

Basic information

• Product Name: Boc-N-methyl-L-leucine
• Synonyms: N-ALPHA-T-BUTYLOXYCARBONYL-N-ALPHA-METHYL-L-LEUCINE;N-ALPHA-T-BUTOXYCARBONYL-N-ALPHA-METHYL-L-LEUCINE;N-ALPHA-T-BUTOXYCARBONYL-BETA-T-BUTYL-L-ALANINE;N-ALPHA-T-BUTOXYCARBONYL-GAMMA-METHYL-L-LEUCINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-N-ALPHA-METHYL-L-LEUCINE;N-ALPHA-T-BOC-N-ALPHA-METHYL-L-LEUCINE;BOC-BETA-TBU-ALANINE;BOC-BETA-TBU-ALA-OH
• CAS NO: 53363-89-6
• Molecular Formula: C₁₂H₂₃NO₄
• Molecular Weight: 245.32
• Product Categories: Amino Acid Derivatives;N-Methyl Amino Acids;amino acids
• Mol File: 53363-89-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: 55-60 °C
• Boiling Point: 338.2 °C at 760 mmHg
• Flash Point: 158.3 °C
• Appearance: White powder
• Density: 1.053 g/cm³
• Vapor Pressure: 1.86E-05mmHg at 25°C
• Refractive Index: 1.466
• Storage Temp.: Store at RT.
• PKA: 4.04±0.21(Predicted)
• BRN: 2373250
• CAS DataBase Reference: Boc-N-methyl-L-leucine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-N-methyl-L-leucine(53363-89-6)
• EPA Substance Registry System: Boc-N-methyl-L-leucine(53363-89-6)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 53363-89-6(Hazardous Substances Data)

Usage

Description

Boc-N-methyl-L-leucine is the BOC (tert-butyloxycarbonyl) protected N-methylated leucine, an amino acid building block used in peptide synthesis. This N-methylated amino acid is valuable in peptide synthesis, as it provides improved properties to peptides, such as increased proteolytic stability, increased membrane permeability, and altered conformation. These effects are significant in the development of therapeutic peptide compounds and the assessment of biological activity in modified peptides. The BOC group can be easily removed by treatment with strong acids like trifluoroacetic acid.

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

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

Downstream Products

• 175087-32-8 Boc-Leu(Me)-OBzl 
• 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 
• 1208162-98-4 N-Me-Leu-OBzl p-toluenesulfonic acid salt 
• 161670-36-6 Boc-Phe(4-OMe)-MeLeu-OH 
• 161670-35-5 Boc-Phe(4-OMe)-MeLeu-OMe 
• 189162-94-5 (3S,4S)-4-((S)-2-{[(S)-2-Amino-3-(4-methoxy-phenyl)-propionyl]-methyl-amino}-4-methyl-pentanoylamino)-3-hydroxy-6-methyl-heptanoic acid [5-(3-methyl-butylcarbamoyl)-pentyl]-amide 
• 161670-37-7 [(S)-1-{[(S)-1-((S)-1-{(S)-1-Hydroxy-2-[5-(3-methyl-butylcarbamoyl)-pentylcarbamoyl]-ethyl}-3-methyl-butylcarbamoyl)-3-methyl-butyl]-methyl-carbamoyl}-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 68898-79-3 ((S)-1-{[2-(4-Hydroxy-phenyl)-ethyl]-methyl-carbamoyl}-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester 
• 68898-84-0 3-[4-(2-{[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyl]-methyl-amino}-ethyl)-phenoxy]-propionic acid 
• 68898-82-8 (E)-3-[4-(2-{[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoyl]-methyl-amino}-ethyl)-phenoxy]-acrylic acid benzyl ester 
• 248922-88-5 (S)-{1-[4,4-bis-(4-fluoro-phenyl)-butylcarbamoyl]-3-methyl-butyl}-methyl-carbamic acid tert-butyl ester 
• 1273317-91-1 (S)-5-isobutyl-1-methyl-3-phenethylimidazolidin-4-one 
• 1393122-05-8 Boc-N-MeLeu-Sar-D-Phe-OMe 
• 1393121-88-4 Boc-N-MeLeu-N-MePhe-NH₂ 

Relevant articles and documents

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.

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.

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.