89536-84-5

Usage

Uses

Used in Peptide Synthesis:
Boc-N-methyl-D-leucine is used as a building block for the synthesis of peptides and peptidomimetics. It is incorporated into peptide chains to introduce the N-methyl-D-leucine moiety, which can alter the conformation and stability of the resulting peptides, potentially enhancing their biological activity or selectivity.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Boc-N-methyl-D-leucine is utilized in the development of bioactive compounds and drugs. Its incorporation into peptide-based therapeutics can lead to the creation of molecules with specific targeting capabilities, improved pharmacokinetics, or novel mechanisms of action.
Used in Protein Structure and Function Studies:
Boc-N-methyl-D-leucine is also used in research settings to study protein structure and function. By introducing this moiety into proteins, scientists can investigate the effects on protein folding, stability, and interactions with other biomolecules, providing insights into protein biology and potential therapeutic targets.
Used in the Development of Specific Protein-Protein Interaction Modulators:
Furthermore, Boc-N-methyl-D-leucine is employed in the design of compounds that modulate specific protein-protein interactions. These interactions are crucial in many biological processes, and their modulation can have significant implications in the treatment of various diseases by affecting cellular signaling pathways.

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-/m1/s1

Upstream product

• 16937-99-8 N-Boc-D-Leu 
• 74-88-4 methyl iodide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 328-38-1 (R)-leucine 

Downstream Products

• 89536-86-7 H-N-Me-D-Leu-OBzl 
• 129919-89-7 N-(tert-butoxycarbonyl)-N-methyl-D-leucine benzyl ester 
• 123593-53-3 (S)-2-{(2R,3R)-3-(4-Allyloxy-3,5-dichloro-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionylamino}-3-cyano-propionic acid 2-trimethylsilanyl-ethyl ester 
• 118171-86-1 Boc-(R)-MeLeu-(S)-Thr(Bzl)-(3S,4R,5S)-Ist-OTce 
• 169825-22-3 (R)-2-[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 
• 189007-66-7 (S)-N-[Bis-(4-methoxy-phenyl)-methyl]-2-[(2R,3R)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-succinamic acid 2-trimethylsilanyl-ethyl ester 
• 185461-51-2 Boc-didemnin A 
• 185461-66-9 (3S,4R,5S)-4-{(2S,3R)-3-Benzyloxy-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-butyrylamino}-3-hydroxy-5-methyl-heptanoic acid methyl ester 
• 207390-81-6 (S)-2-[(2R,3R)-2-[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester 
• 207390-96-3 C₅₉H₇₃BrClFN₈O₁₇Si 
• 218915-03-8 (2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid ethyl ester 
• 1208162-98-4 H-N-Me-D-Leu-OBzl p-toluenesulfonic acid salt 
• 863781-46-8 (R)-2-[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester 
• 909108-67-4 (S)-2-[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester 

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.

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.

HETEROCYCLIC KINASE INHIBITORS

The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

Efficient total synthesis of didemnins A and B

Didemnins A and B (1 and 2), cytotoxic cyclic peptides from a Caribbean tunicate Trididemnum solidum, have been efficiently prepared by a convergent scheme from two key eastern and western fragments. Efficient routes to derivatives of the constituents of didemnis were explored. Benzyl (2RS,4S)-[O-(tert-butyldimethylsilyl)hydroxyisovaleryl]propionate (Hip derivative) was prepared from 2-hydroxyisovaleric acid by use of C-acylation of Meldrum's acid with diethyl phosphorocyanidate as a key step. Derivatives of (3S,4R,5S)-isostatine (Ist) were prepared from Boc-(R)-alloisoleucine. Methylation of Boc-(R)-Leu-OH and Z-(S)-Tyr-OH respectively afforded the corresponding N-methyl and N,O-dimethyl derivatives. The key eastern fragment, (2RS,4S)-Hip-(S)-Leu-(S)-Pro-OBzl (3), was prepared stepwise from (S)-Pro-OBzl, while Boc-(R)-MeLeu-(S)-Thr[Z-(S)-MeTyr(Me)]-(3S,4R,5S)-Ist(TBDMS)-OH (4), the key western fragment for didemnin A (1), was prepared from Ist derivatives. Coupling of 3 with 4 and cyclization, followed by deprotection, afforded didemnin A (1), which was converted to didemnin B (2).