128424-93-1

Basic information

• Product Name: L-Leucine, N-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-
• CAS NO: 128424-93-1
• Molecular Formula: C15H21N5O7
• Molecular Weight: 383.361
• Mol File: 128424-93-1.mol

Chemical Properties

• CAS DataBase Reference: L-Leucine, N-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Leucine, N-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(128424-93-1)
• EPA Substance Registry System: L-Leucine, N-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(128424-93-1)

Safety Data

• Hazardous Substances Data: 128424-93-1(Hazardous Substances Data)

Upstream product

• 61-90-5 L-leucine 
• 95713-52-3 N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide 
• 2873-36-1 cyclo(L-Pro-L-Leu) 

Relevant articles and documents

Mariannamides A and B, new cyclic octapeptides isolated from Mariannaea elegans NBRC102301

Two new cyclic octapeptides, mariannamides A (1) and B (2), have been isolated from Mariannaea elegans NBRC102301, a Pinus densiflora-derived filamentous fungus. Their structures were elucidated to be cyclo-(L-Leu1-L-Pro1-L-Pro2-L-Leu2-L-Ile1-L-Pro3-L-Val1-L-Ile2) and cyclo-(L-Leu1-L-Pro1-L-Pro2-L-Leu2-L-Ile1-L-Pro3-L-Val1-L-Val2) based on spectroscopic data and Marfey's method. Mariannamide A (1) promoted mRNA expression of sirtuin 1 (SIRT1) in C2C12 cells, a mouse skeletal muscle myoblast cell line, and showed the antimicrobial activity against Escherichia coli and Cryptococcus neoformans.

Eight linear peptides from the deep-sea-derived fungus Simplicillium obclavatum EIODSF 020

Eight new linear peptides, simplicilliumtides A-H (1-8) were isolated from a culture broth of the deep-sea-derived fungal strain Simplicillium obclavatum EIODSF 020. Their structures were elucidated by spectroscopic analysis, and their absolute configurat

Cyclic tetrapeptides from the marine strain Streptomyces sp. PNM-161a with activity against rice and yam phytopathogens

Two cyclotetrapeptides, henceforth named Provipeptides A (1) and B (2), along with five known diketopiperazines (3–7) were isolated from the liquid culture of marine Streptomyces sp. 161a recovered from a sample of sea grass Bryopsis sp. The structures of cyclotetrapeptides and diketopiperazines (DKPs) were established by 1D and 2D NMR data, MS, and by comparison with literature data. The absolute stereochemistry of compounds cyclo-(l-Pro-l-Leu-d-Pro-l-Phe) 1 and cyclo-(-Pro-Ile-Pro-Phe) 2 was established by the Marfey’s method. Compound 1 showed antibacterial activity against rice phytopathogenic strains Burkholderia glumae (MIC = 1.1 mM) and Burkholderia gladioli (MIC = 0.068 mM), compound 2 was active only against B. glumae (MIC = 1.1 mM), and DKP cyclo-[l-Pro-l-Leu] 5 showed to be active against B. gladioli (MIC = 0.3 mM) and B. glumae (MIC = 2.4 mM). Compounds 1 and 2 showed 65% and 50% inhibition of Colletotrichum gloeosporioides (yam pathogen) conidia germination, respectively at a concentration of 1.1 mM.

Puromycins B-E, Naturally Occurring Amino-Nucleosides Produced by the Himalayan Isolate Streptomyces sp. PU-14G

The isolation and structure elucidation of four new naturally occurring amino-nucleoside [puromycins B-E (1-4)] metabolites from a Himalayan isolate (Streptomyces sp. PU-14-G, isolated from the Bara Gali region of northern Pakistan) is reported. Consistent with prior reports, comparative antimicrobial assays revealed the need for the free 2″-amine for anti-Gram-positive bacteria and antimycobacterial activity. Similarly, comparative cancer cell line cytotoxicity assays highlighted the importance of the puromycin-free 2″-amine and the impact of 3′-nucleoside substitution. These studies extend the repertoire of known naturally occurring puromycins and their corresponding SAR. Notably, 1 represents the first reported naturally occurring bacterial puromycin-related metabolite with a 3′-N-amino acid substitution that differs from the 3′-N-tyrosinyl of classical puromycin-type natural products. This discovery suggests the biosynthesis of 1 in Streptomyces sp. PU-14G may invoke a uniquely permissive amino-nucleoside synthetase and/or multiple synthetases and sets the stage for further studies to elucidate, and potentially exploit, new biocatalysts for puromycin chemoenzymatic diversification.

Cytotoxic Orbitide from the Latex of Croton urucurana

The bioactive ethyl acetate phase obtained from the latex of Croton urucurana Baillon afforded a novel orbitide (1), [1-9-NαC]-crourorb A1, that proved active against NCI-ADR/RES (ovary, multidrug-resistance phenotype) cells with the same potency as doxor

A new cyclopeptide and other constituents from the leaves of Zanthoxylum rigidum Humb. & Bonpl. ex Willd. (Rutaceae)

A new cyclopeptide, cyclozanthoxylane A (1), the lignans cis- and trans-methylpluviatolide, the flavonoid isoquercitrin, along with a mixture of benzoic and cinnamic acid derivatives, were isolated from the MeOH extract of the leaves of Zanthoxylum rigidum (Rutaceae). The structures of the compounds were determined on the basis of 1D- and 2D-NMR, and MS analysis. It is the first time that a natural cyclic peptide has been isolated from the genus Zanthoxylum.

Auyuittuqamides A-D, Cyclic Decapeptides from Sesquicillium microsporum RKAG 186 Isolated from Frobisher Bay Sediment

Four new cyclic decapeptides, auyuittuqamides A-D (1-4), were obtained from Sesquicillium microsporum RKAG 186 obtained from marine sediment collected from the intertidal zone of Frobisher Bay, Nunavut, Canada. The structures of the compounds were elucida

Sungsanpin, a lasso peptide from a deep-sea streptomycete

Sungsanpin (1), a new 15-amino-acid peptide, was discovered from a Streptomyces species isolated from deep-sea sediment collected off Jeju Island, Korea. The planar structure of 1 was determined by 1D and 2D NMR spectroscopy, mass spectrometry, and UV spectroscopy. The absolute configurations of the stereocenters in this compound were assigned by derivatizations of the hydrolysate of 1 with Marfey's reagents and 2,3,4,6-tetra-O-acetyl-β-d- glucopyranosyl isothiocyanate, followed by LC-MS analysis. Careful analysis of the ROESY NMR spectrum and three-dimensional structure calculations revealed that sungsanpin possesses the features of a lasso peptide: eight amino acids (-Gly1-Phe-Gly-Ser-Lys-Pro-Ile-Asp8-) that form a cyclic peptide and seven amino acids (-Ser9-Phe-Gly-Leu-Ser-Trp-Leu 15) that form a tail that loops through the ring. Sungsanpin is thus the first example of a lasso peptide isolated from a marine-derived microorganism. Sungsanpin displayed inhibitory activity in a cell invasion assay with the human lung cancer cell line A549.

Bioactive compounds from the aerial parts of brachystemma calycinum and structural revision of an octacyclopeptide

Four new cyclic peptides, brachystemins F - I (1 - 4), and 11 known compounds were isolated from the aerial parts of Brachystemma calycinum. The absolute configurations of compounds 1 - 4 were assigned using Marfey's method. The structure of compound 5 was revised from cyclo(Pro1 - Phe 2 - Leu3 - Ala4 - Thr5 - Pro 6 - Ala7 - Gly8) to cyclo(Pro1 - Pro2 - Ala3 - Gly4 - Leu5 - Ala 6 - Thr7 - Phe8) with QTOF/MS and X-ray diffraction analysis. The N-containing compounds were assessed for their inhibitory effects on the secretion of monocyte chemokine ligand 2 (CCL-2), interleukin 6 (IL-6), and collagen IV against high-glucose-stimulated mesangial cells. Compound 5 was evaluated for its effects on collagen I, reactive oxygen species (ROS), superoxide anion (O2?-) production, and cell viability in mesan ial cells, and on nitric oxide (NO) production in macrophage cells.

New cyclic tetrapeptides and asteltoxins from gorgonian-derived fungus Aspergillus sp. SCSGAF 0076

Three new cyclic tetrapeptides, aspergillipeptides A-C (1-3), and one new asteltoxin B (4) were isolated from a culture broth of gorgonian-derived fungal strain Aspergillus sp. SCSGAF 0076. Their structures were elucidated by spectroscopic analysis, and the absolute configurations of aspergillipeptides A-C were determined by Marfey's method. Aspergillide C (3) showed strong antifouling activity against Bugula neritina larvae settlement with LC 50/EC50>25.