4818-03-5

Basic information

• Product Name: L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester
• CAS NO: 4818-03-5
• Molecular Formula: C21H32N2O5
• Molecular Weight: 392.495
• Mol File: 4818-03-5.mol

Chemical Properties

• CAS DataBase Reference: L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester(4818-03-5)
• EPA Substance Registry System: L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester(4818-03-5)

Safety Data

• Hazardous Substances Data: 4818-03-5(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester is used as a building block in peptide synthesis for the creation of complex peptide structures. Its incorporation into peptides allows for the development of novel therapeutic agents and bioactive molecules.
Used in Protein Engineering:
In the field of protein engineering, L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester is utilized as a component in the design and modification of proteins. This enables the enhancement of protein functions and the generation of proteins with desired properties for various applications.
Used in Drug Development:
L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester serves as a study tool in the development of new drugs and therapies. Its unique chemical and biological properties make it a promising candidate for the exploration of potential therapeutic effects and mechanisms of action.
Used in Biochemistry Research:
In biochemistry, L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester is employed as a research compound to investigate the interactions between peptides and other biomolecules. This helps in understanding the fundamental processes of biological systems and the potential for new therapeutic interventions.
Used in Biotechnology Applications:
L-Leucine, N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-, methyl ester has potential applications in biotechnology, where it can be used to develop novel bioproducts and bioprocesses. Its unique properties may contribute to the advancement of biotechnological solutions in various industries, such as agriculture, environmental management, and industrial biotechnology.

Upstream product

• 2666-93-5 (S)-Leu-OMe 
• 3160-59-6 N-Cbz-L-Isoleucine 
• 3391-99-9 N-Z-L-isoleucine N-hydroxysuccinimide ester 
• 7517-19-3 methyl (L)-leucinate hydrochloride 

Downstream Products

• 1359857-21-8 Fmoc-Lys(Z)-Ile-Leu-OMe 
• 26462-22-6 Ile-Leu 
• 173739-69-0 Z-Gly-L-Leu-Aib-(Gly)2-L-Leu-Aib-Gly-L-Ile-L-Leu-OMe 
• 176664-82-7 C₄₇H₇₇N₉O₁₂ 
• 176664-80-5 (S)-2-((2S,3S)-2-{2-[2-((S)-2-{2-[2-(2-Benzyloxycarbonylamino-2-methyl-propionylamino)-acetylamino]-acetylamino}-4-methyl-pentanoylamino)-2-methyl-propionylamino]-acetylamino}-3-methyl-pentanoylamino)-4-methyl-pentanoic acid methyl ester 
• 176664-78-1 Z-Gly-Gly-Leu-Aib-Gly-Ile-Leu-OMe 
• 176664-76-9 (S)-2-[(2S,3S)-2-(2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-4-methyl-pentanoylamino]-2-methyl-propionylamino}-acetylamino)-3-methyl-pentanoylamino]-4-methyl-pentanoic acid methyl ester 
• 176664-74-7 (S)-2-((2S,3S)-2-{2-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-2-methyl-propionylamino]-acetylamino}-3-methyl-pentanoylamino)-4-methyl-pentanoic acid methyl ester 
• 156916-67-5 Z-Aib-Gly-L-Ile-L-Leu-OMe 
• 119768-10-4 Z-Gly-L-Ile-L-Leu-OMe 
• 38972-95-1 N-Benzyloxycarbonyl-L-isoleucyl-L-leucin 

Relevant articles and documents

Trichogin GA IV: A versatile template for the synthesis of novel peptaibiotics

Trichogin GA IV, isolated from the fungus Trichoderma longibrachiatum, is the prototype of lipopeptaibols, the sub-class of short-length peptaibiotics exhibiting membrane-modifying properties. This peptaibol is predominantly folded in a mixed 310-/α-helical conformation with a clear, albeit modest, amphiphilic character, which is likely to be responsible for its capability to perturb bacterial membranes and to induce cell death. In previous papers, we reported on the interesting biological properties of trichogin GA IV, namely its good activity against Gram positive bacteria, in particular methicillin-resistant S. aureus strains, its stability towards proteolytic degradation, and its low hemolytic activity. Aiming at broadening the antimicrobial activity spectrum by increasing the peptide helical amphiphilicity, in this work we synthesized, by solution and solid-phase methodologies, purified and fully characterized a set of trichogin GA IV analogs in which the four Gly residues at positions 2, 5, 6, 9, lying in the poorly hydrophilic face of the helical structure, are substituted by one (position 2, 5, 6 or 9), two (positions 5 and 6), three (positions 2, 5, and 9), and four (positions 2, 5, 6, and 9) Lys residues. The conformational preferences of the Lys-containing analogs were assessed by FT-IR absorption, CD and 2D-NMR techniques in aqueous, organic, and membrane-mimetic environments. Interestingly, it turns out that the presence of charged residues induces a transition of the helical conformation adopted by the peptaibols (from 3 10-to α-helix) as a function of pH in a reversible process. The role played in the analogs by the markedly increased amphiphilicity was further tested by fluorescence leakage experiments in model membranes, protease resistance, antibacterial and antifungal activities, cytotoxicity, and hemolysis. Taken together, our biological results provide evidence that some of the least substituted among these analogs are good candidates for the development of new membrane-active antimicrobial agents. The Royal Society of Chemistry 2012.