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Upstream product

• 95713-52-3 N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide 
• 1232889-28-9 sclerotiotide A 
• 1232889-32-5 sclerotiotide B 
• 1232889-36-9 sclerotiotide C 
• 1259395-30-6 anabaenopeptin MM₈₂₃ 
• 1259395-31-7 anabaenopeptin MM₈₅₀ 
• 1255709-51-3 7,39-epi-Lagunamide A 
• 1255709-52-4 lagunamide B 
• 3913-67-5 N-methylalanine 
• 95713-52-3 (1-fluoro-2,4-dinitrophenyl)-5-L-alanine amide 
• 600-21-5 N-methylalanine 
• 1314917-07-1 cyclo(N-methyl-L-alanyl-N-methyl-L-alanyl-2-aminobenzoyl-L-alanyl-2-aminobenzoyl) 
• 1314917-05-9 cyclo(L-alanyl-N-methyl-L-alanyl-2-aminobenzoyl-N-methyl-L-alanyl-2-aminobenzoyl) 

Relevant academic research and scientific papers

Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.

The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the 26-membered cyclodepsipeptide odoamide (1). The gross structure of 1 was determined by 1D and 2D NMR analyses, whereas its absolute stereochemistry was determined using a variety of different methods, including synthesis and chemical degradation followed by chiral HPLC analysis. Notably, odoamide (1) showed potent cytotoxicity against HeLa S3 human cervical cancer cells with an IC50value of 26.3?nM.

Evolved diversification of a modular natural product pathway: Apratoxins F and G, two cytotoxic cyclic depsipeptides from a palmyra collection of Lyngbya bouillonii

A collection of Lyngbya bouillonii from Palmyra Atoll in the Central Pacific, a site several thousand kilometers distant from all previous collections of this chemically prolific species of cyanobacterium, was found to contain two new cancer cell cytotoxins of the apratoxin family. The structures of the new compounds, apratoxins F and G, were determined by 1D and 2D NMR techniques in combination with mass spectrometric methods. Stereochemistry was explored by using chromatographic analyses of the hydrolytically released fragments in combination with NMR and optical rotation comparisons with known members of the apratoxin family. Apratoxins F and G add fresh insights into the SAR of this family because they incorporate an N-methyl alanine residue at a position where all prior apratoxins have possessed a proline unit, yet they retain high potency as cytotoxins to H-460 cancer cells with IC50 values of 2 and 14 nM, respectively. Additional assays using zone inhibition of cancer cells and clonogenic cells give a comparison of the activities of apratoxin F to apratoxin A. Additionally, the clonogenic studies in combination with maximum tolerated dose (MTD) studies provided insights as to dosing schedules that should be used for in vivo studies, and preliminary in vivo evaluation validated the predicted in vivo efficacy for apratoxin A. These new apratoxins are illustrative of a mechanism (the modification of an NRPS adenylation domain specificity pocket) for evolving a biosynthetic pathway so as to diversify the suite of expressed secondary metabolites.

Polyketides and nitrogenous metabolites from the endophytic fungus Phomopsis sp. D15a2a

Three new polyketides, phomopones A?C (1–3), one new cyclic tetrapeptide, 18-hydroxydihydrotentoxin (4), and a new amide, 6-hydroxyenamidin (5) together with a known derivative, enamindin (6) were obtained from the endophytic fungus Phomopsis sp. D15a2a i

Two new cyclic pentapeptides from the marine-derived fungus aspergillus versicolor

Two new cyclic pentapeptides, named versicotides A (1) and B (2), were obtained from a marine-derived fungus strain ZLN-60, identified as Aspergillus versicolor. Their structures were established on the basis of chemical and spectroscopic evidence. Versic

Gymnopeptides A and B, Cyclic Octadecapeptides from the Mushroom Gymnopus fusipes

Mycochemical study of the mushroom Gymnopus fusipes led to the discovery of two new cyclopeptides. The two compounds, named as gymnopeptides A and B, are unprecedented highly N-methylated cyclic octadecapeptides. Detailed spectroscopic studies, Marfey's analysis, and a preliminary molecular modeling study suggested that both are natural cyclic β hairpins. The isolated compounds exhibited striking antiproliferative activity on several human cancer cell lines, with nanomolar IC50 values.

Friomaramide, a Highly Modified Linear Hexapeptide from an Antarctic Sponge, Inhibits Plasmodium falciparum Liver-Stage Development

The cold waters of Antarctica are known to harbor a rich biodiversity. Our continuing interest in the chemical analysis of Antarctic invertebrates has resulted in the isolation of friomaramide (1), a new, highly modified hexapeptide, from the Antarctic sponge Inflatella coelosphaeroides. The structure of friomaramide was determined using spectroscopic methods and its configuration established by Marfey's method. Friomaramide, which bears the unusual permethylation of the amino acid backbone and is the longest polypeptide bearing a tryptenamine C-terminus, blocks >90% of Plasmodium falciparum liver-stage parasite development at 6.1 μM.

C3 and 2D C3 Marfey's Methods for Amino Acid Analysis in Natural Products

We validate the improved resolution and sensitivity of the C3 Marfey's method, including an ability to resolve all Ile isomers, against an array of amino acids commonly encountered in natural products and by comparison to an existing Marfey's m

Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium

Janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 μM.

Jahanyne, an apoptosis-inducing lipopeptide from the marine cyanobacterium lyngbya sp.

An acetylene-containing lipopeptide, jahanyne, was isolated from the marine cyanobacterium Lyngbya sp. Its gross structure was established by spectroscopic analyses, and the absolute configuration was clarified based on a combination of chiral HPLC analyses, spectroscopic analyses, and derivatization reactions. Jahanyne significantly inhibited the growth of human cancer cells and induced apoptosis in HeLa cells.

Psychrophilins E-H and versicotide C, cyclic peptides from the marine-derived fungus aspergillus versicolor ZLN-60

Four new cyclic peptides, psychrophilins E-H (1-4), possessing a rare amide linkage between the carboxylic acid in anthranilic acid (ATA) and the nitrogen from an indole moiety, along with a new ATA-containing hexapeptide, versicotide C (5), were obtained from the culture of the marine-derived fungus Aspergillus versicolor ZLN-60. The structures, including absolute configurations, were elucidated by a combination of HRESIMS, NMR, X-ray crystallography, TDDFT ECD calculations, and Marfeys method. Versicotide C (5) is the first natural cyclic hexapeptide containing two anthranilic acids. Compounds 1-5 were not cytotoxic, and compound 3 showed potent lipid-lowering effects.