128425-06-9

Basic information

• Product Name: D-Leucine, N-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-
• CAS NO: 128425-06-9
• Molecular Formula: C15H21N5O7
• Molecular Weight: 383.361
• Mol File: 128425-06-9.mol
• Article Data: 34

Chemical Properties

• CAS DataBase Reference: D-Leucine, N-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Leucine, N-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(128425-06-9)
• EPA Substance Registry System: D-Leucine, N-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(128425-06-9)

Safety Data

• Hazardous Substances Data: 128425-06-9(Hazardous Substances Data)

Upstream product

• 328-38-1 (R)-leucine 
• 95713-52-3 N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide 
• 328-39-2 LEUCINE 
• 194660-14-5 desotamide A 
• 131956-33-7 depsidomycin B 

Relevant articles and documents

Anti-inflammatory activity of a new cyclic peptide, citrusin XI, isolated from the fruits of Citrus unshiu

Ethnopharmacological relevance Citrus unshiu (Rutaceae) is an easy-peeling citrus fruit, which has been used as a traditional Korean medicine for improving skin elasticity, relieving fatigue and cough, and preventing bronchitis, flu, and various cancers. However, its active components associated with anti-inflammation and underlying mechanisms remain unknown. In this study, we investigated the active constituents from the fruits of Citrus unshiu and evaluated the anti-inflammatory activity in order to support the traditional usage of Citrus unshiu. Material and methods Repeated column chromatography, together with a semi-preparative HPLC purification was used to separate the bioactive constituent from the EtOAc soluble fraction of the EtOH extract of Citrus unshiu fruits. Anti-inflammatory effects of the isolated compounds on lipopolysaccharide (LPS)-induced production of pro-inflammatory mediators were examined using RAW264.7 macrophage cells. Results A new cyclic peptide, citrusin XI (1), was isolated and identified from the fruits of Citrus unshiu. The structure of compound 1 was elucidated by spectroscopic analysis, including 1D and 2D nuclear magnetic resonance (NMR) (1H, 13C, COSY, HMQC and HMBC experiments), and high resolution (HR)-mass spectrometry, and its absolute configurations were further confirmed by the Marfeys method. Compound 1 decreased NO production in LPS-stimulated RAW264.7 cells in a dose-dependent manner with an IC50 value of 70 μM. Compound 1 suppressed NO production by decreasing iNOS expression but COX-2 expression was slightly associated with the reduction by compound 1 in LPS-induced RAW264.7 cells. Furthermore, compound 1 inhibited NF-κB activation by blocking IκBα degradation and NF-κB phosphorylation in LPS-stimulated RAW264.7 cells. Conclusions These results indicate that a new cyclic peptide, citrusin XI, from Citrus unshiu fruits has anti-inflammatory properties that inhibit the release of pro-inflammatory mediators. Compound 1 decreases NO production by decreasing iNOS expression and NF-κB activation associated with IκBα degradation and NF-κB phosphorylation in LPS-induced RAW264.7 cells. This is the first study to clarify the underlying mechanism of the anti-inflammatory effect exerted by a pure isolated compound from Citrus unshiu in LPS-stimulated RAW264.7 macrophage cells. The phytochemical, citrusin XI of Citrus unshiu may serve as lead compound in the design of new agents for preventing and treating inflammatory diseases.

Nicrophorusamides A and B, Antibacterial Chlorinated Cyclic Peptides from a Gut Bacterium of the Carrion Beetle Nicrophorus concolor

Nicrophorusamides A and B (1 and 2) were discovered from a rare actinomycete, Microbacterium sp., which was isolated from the gut of the carrion beetle Nicrophorus concolor. The structures of the nicrophorusamides were established as new chlorinated cyclic hexapeptides bearing uncommon amino acid units mainly based on 1D and 2D NMR spectroscopic analysis. The absolute configurations of the amino acid residues 5-chloro-l-tryptophan, d-threo-β-hydroxyasparagine/d-asparagine, l-ornithine, l-allo-isoleucine, d-leucine, and d-valine were determined using Marfey's method and chemical derivatization with 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate followed by LC/MS analysis. Nicrophorusamide A (1) showed antibacterial activity against several Gram-positive bacteria.

3-Hydroxy-4-methyldecanoic Acid-Containing Cyclotetradepsipeptides from an Endolichenic Beauveriasp.

An investigation of an endolichenicBeauveriasp. led to the discovery of seven new cyclotetradepsipeptides, beauveamides A-G (2-8), along with the known beauverolide Ka (1). All incorporate a 3-hydroxy-4-methyldecanoic acid (HMDA) moiety in their structures. Their configuration was determined through Marfey’s,J-based configuration analysis, and NMR computational methods, representing the first time that the stereostructures of HMDA-moiety-containing cyclotetradepsipeptides have been established. Compounds1and2exhibited protecting effects on HEI-OC1 cells at 10 μM, while14, and5could stimulate glucose uptake in cultured rat L6 myoblasts at 50 μM. Compound1showed dose-dependent activity in both L6 myoblasts and myotubes.

Leveraging Peptaibol Biosynthetic Promiscuity for Next-Generation Antiplasmodial Therapeutics

Malaria remains a worldwide threat, afflicting over 200 million people each year. The emergence of drug resistance against existing therapeutics threatens to destabilize global efforts aimed at controlling Plasmodium spp. parasites, which is expected to leave vast portions of humanity unprotected against the disease. To address this need, systematic testing of a fungal natural product extract library assembled through the University of Oklahoma Citizen Science Soil Collection Program has generated an initial set of bioactive extracts that exhibit potent antiplasmodial activity (EC50 25 μM, selectivity index > 250). The unique chemodiversity afforded by these fungal isolates serves to unlock new opportunities for translating peptaibols into a bioactive scaffold worthy of further development.

Linear Peptides Containing d -Leucine with Neuroprotective Activities from the Leech Whitmania pigra Whitman

Three new linear peptides containing d-leucine, named whitmantides A-C (1-3), were isolated from the dried whole bodies of Whitmania pigra Whitman. Their structures with absolute configurations were elucidated by Edman degradation, mass spectrometry, Marf