73401-65-7

Usage

Uses

Used in Pharmaceutical Research and Development:
BOC-LEU-LEU-OH is used as a research tool for investigating the biological functions and medicinal properties of peptides containing leucine residues. Its protective BOC group allows for controlled peptide synthesis, facilitating the study of peptide interactions and their potential therapeutic applications.
Used in Drug Synthesis:
In the pharmaceutical industry, BOC-LEU-LEU-OH serves as a building block for the synthesis of therapeutic peptides. The BOC group ensures the selective protection of the amine group, enabling the stepwise assembly of complex peptide structures with leucine residues, which can be crucial for the development of new drugs with specific biological activities.
Used in Protein Synthesis Studies:
BOC-LEU-LEU-OH is employed in research to understand the role of leucine in protein synthesis and its impact on protein metabolism regulation. This knowledge can contribute to the development of treatments for various diseases related to protein synthesis and metabolism disorders.
Used in Peptide-based Drug Delivery Systems:
BOC-LEU-LEU-OH can be incorporated into peptide-based drug delivery systems, where its hydrophobic nature and the protective BOC group can enhance the stability and bioavailability of therapeutic agents. This application can improve the efficacy and targeting of drugs in the treatment of various diseases.

Upstream product

• 3392-09-4 Boc-Leu-ONSu 
• 61-90-5 L-leucine 
• 32925-57-8 Boc-Leu-Leu-OBzl 
• 38155-18-9 L-leucyl-L-phenylalanine methyl ester 
• 15136-32-0 (N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester 
• 863781-33-3 Boc-Val-Leu-Phe-OMe 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 2666-93-5 (S)-Leu-OMe 
• 2743-40-0 L-leucine ethyl ester hydrochloride 
• 15136-13-7 N-tert-butoxycarbonyl-L-leucyl-L-leucine methyl ester 
• 83610-39-3 N-(N-tert-butoxycarbonyl-L-leucyl)-L-leucine ethyl ester 

Downstream Products

• 3303-31-9 L-leucyl-L-leucine 
• 863781-59-3 (S)-2-(2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-3-methyl-butyrylamino}-acetylamino)-3-phenyl-propionic acid methyl ester 
• 863781-61-7 (S)-2-[2-({(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-3-methyl-butyryl}-methyl-amino)-acetylamino]-3-phenyl-propionic acid methyl ester 
• 863781-40-2 (S)-2-[(S)-2-({(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-3-methyl-butyryl}-methyl-amino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester 
• 863781-51-5 (S)-2-[(S)-2-((S)-2-{[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoyl]-methyl-amino}-3-methyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester 
• 863781-34-4 (S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-3-methyl-butyrylamino}-4-methyl-pentanoylamino)-3-phenyl-propionic acid methyl ester 
• 926661-02-1 C₄₉H₇₅N₇O₁₁ 
• 1038867-01-4 C₄₄H₆₇N₇O₉ 
• 926661-03-2 C₅₉H₉₃N₉O₁₃ 
• 934715-80-7 2-(2-{2-[2-(2-amino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-butyrylamino}-4-methyl-pentanoylamino)-3-phenyl-propionic acid 
• 934715-78-3 2-(2-{2-[2-(2-amino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-butyrylamino}-4-methyl-pentanoylamino)-3-phenyl-propionic acid 
• 934715-77-2 2-(2-{2-[2-(2-amino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-3-methyl-butyrylamino}-3-phenyl-propionylamino)-3-phenyl-propionic acid 
• 934715-76-1 2-[2-({2-[2-(2-amino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-3-methyl-butyryl}-methyl-amino)-3-phenyl-propionylamino]-3-phenyl-propionic acid 
• 934715-38-5 3-benzyl-6-benzyloxymethyl-12,15-diisobutyl-9-isopropyl-1,4,7,10,13pentaaza-cyclopentadecane-2,5,8,11,14-pentaone 

Relevant academic research and scientific papers

Synthesis and biological evaluation of curcumin derivatives with water-soluble groups as potential antitumor agents: An in vitro investigation using tumor cell lines

Three series of curcumin derivatives including phosphorylated, etherified, and esterified products of curcumin were synthesized, and their anti-tumor activities were assessed against human breast cancer MCF-7, hepatocellular carcinoma Hep-G2, and human cervical carcinoma HeLa cells. Compared with curcumin, compounds 3, 8, and 9 exhibited stronger antitumor cell line growth activities against HeLa cells. Compound 12 also showed higher antitumor cell line growth activities on MCF-7 cells than curcumin. Among them, 4-((1E,6E)-7-(4-Hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl)-2-methoxyphenyl dihydrogen phosphate(3) showed the strongest activity with an half maximal inhibitory concentration (IC50) of 6.78 μM against HeLa cells compared with curcumin with an IC50 of 17.67 μM. Stabilities of representatives of the three series were tested in rabbit plasma in vitro, and compounds 3 and 4 slowly released curcumin inplasma. The effect of compound 3 on HeLa cell apoptosis was determined by examining morphological changes by DAPI (4′,6-diamidino-2-phenylindole) staining as well as Annexin V-FITC/Propidium Iodide (PI) double staining and flow cytometry. The results showed that 3 induced cellular apoptosis in a dose-dependent manner. Together our findings show that 3 merits further investigation as a new potential antitumor drug candidate.

Isolation, structure elucidation and total synthesis of lajollamide a from the marine fungus Asteromyces cruciatus

The marine-derived filamentous fungus Asteromyces cruciatus 763, obtained off the coast of La Jolla, San Diego, USA, yielded the new pentapeptide lajollamide A (1), along with the known compounds regiolone (2), hyalodendrin (3), gliovictin (4), 1N-norgliovicitin (5), and bis-N-norgliovictin (6). The planar structure of lajollamide A (1) was determined by Nuclear Magnetic Resonance (NMR) spectroscopy in combination with mass spectrometry. The absolute configuration of lajollamide A (1) was unambiguously solved by total synthesis which provided three additional diastereomers of 1 and also revealed that an unexpected acid-mediated partial racemization (2:1) of the L-leucine and L-N-Me-leucine residues occurred during the chemical degradation process. The biological activities of the isolated metabolites, in particular their antimicrobial properties, were investigated in a series of assay systems.

Design and synthesis of Hsp90 inhibitors: Exploring the SAR of Sansalvamide A derivatives

Utilizing the structure-activity relationship we have developed during the synthesis of the first two generations and mechanism of action studies that point to the interaction of these molecules with the key oncogenic protein Hsp90, we report here the design of 32 new Sansalvamide A derivatives and their synthesis. Our new structures, designed from previously reported potent compounds, were tested for cytotoxicity on the HCT116 colon cancer cell line, and their binding to the biological target was analyzed using computational studies involving blind docking of derivatives using Autodock. Further, we show new evidence that our molecules bind directly to Hsp90 and modulate Hsp90's binding with client proteins. Finally, we demonstrate that we have integrated good ADME properties into a new derivative.

From peptides to their alternating ester-urea analogues: Synthesis and influence of hydrogen bonding motif and stereochemistry on aggregation

(Chemical Equation Presented) Peptide-mimicking scaffolds with an incorporated ester-urea motif, replacing two adjacent amide residues, were synthesized and their aggregation behavior was studied in dependence of hydrogen bonding sites as well as backbone stereochemistry. Two oligomer series containing either 50% or 100% ester-urea units and either all-(L) or (D)-alt-(L) backbone configuration were prepared via ester and amide couplings, using a divergent/convergent exponential growth strategy. Their aggregation behavior in organic solution was investigated by means of concentration-dependent NMR spectroscopy and compared to the parent peptide series. Interestingly, the naturally occurring peptide scaffold exhibits the largest tendency to associate in combination with the strongest difference in aggregation behavior between all-(L) and (D)-alt-(L) backbone stereochemistry. With increasing incorporation of the ester-urea motif the aggregation strength decreases and become much less dependent on the backbone configuration. The obtained structure-aggregation relationships reveal the importance of the commensurability and multivalency of hydrogen bonding sites as well as conformational restriction for peptide association and should hence aid the design of peptide mimics, such as β -sheet breakers or gelators. 2009 American Chemical Society.

Comprehensive study of sansalvamide A derivatives and their structure-activity relationships against drug-resistant colon cancer cell lines

We report an extensive structure-activity relationship (SAR) of 62 compounds active against two drug-resistant colon cancer cell lines. Our comprehensive evaluation of two generations of compounds utilizes SAR, NMR, and molecular modeling to evaluate the

Synthesis and cytotoxicity of a new class of potent decapeptide macrocycles

(Chemical Equation Presented) Described are the syntheses of five decapeptides that are C-2-symmetrical derivatives of the natural product pentapeptide sansalvamide A. Derivatives were made using a succinct convergent synthesis. These analogues share no s

A templating approach for monodisperse self-assembled organic nanostructures

The precise structural control is known for self-assembly into closed spherical structures (e.g., micelles), but similar control of open structures is much more challenging. Inspired by natural tobacco mosaic virus, we present the use of a rigid-rod template to control the size of a one-dimensional self-assembly. We believe that this strategy is novel for organic self-assembly and should provide a general approach to controlling size and dimension. Copyright

MACROCYCLIC PEPTIDES AND METHODS FOR MAKING AND USING THEM

The invention provides novel macrocyclic peptides and methods for their preparation. The invention also provides pharmaceutical compositions and methods to treat, prevent or ameliorate a cell proliferative disease or conditions, e.g., a cancer, in a subje

Synthesis of second-generation Sansalvamide A derivatives: Novel templates as potential antitumor agents

We report the synthesis of 34 second-generation Sansalvamide A derivatives. San A derivatives have unique anticancer properties and target multiple cancers, including colon, pancreatic, breast, prostate, and melanoma. As novel templates, the derivatives d

Synthesis, crystal structure, and coordination properties of a helical peptide having β-(3-pyridyl)-l-alanine and l-glutamic acid residues

A novel helical peptide containing β-(3-pyirdyl)-l-alanine (Pal) and l-glutamic acid (Glu) residues has been designed and successfully prepared as a model ligand of metalloenzyme active sites. The helical peptide, Boc-Leu-Aib-Glu-Leu-Leu-Pal-Aib-Leu-OEt (1) (Boc = tert-butoxycarbonyl, Aib = 2-aminoisobutylic acid) yields fine crystals as an acetnitrile solvate. The metal ion binding affinities of 1 were tested for CoCl2 using UV/vis, CD, Raman, and 1H NMR spectroscopies. The non-linear fitting calculations have revealed the 1:1 complex for CoCl2 with the binding constant 3.6 (±0.7) × 102 M-1.