Three protected tetrapeptides

The structures of three protected tetrapeptides, containing the Boc-Gly-Gly-Phe-X-OMe chain, tert-butoxycarbonyl-glycy-glycl-phenylalanine-leucine methyl ester dihydrate, Boc-Gly-Gly-L-Phe-D-Leu-OMe, C25H38N4O7·2H2O, tert-butoxycarbonyl-glycy-glycl-phenylalanine-methionine methyl ester dihydrate, Boc-Gly Gly-L-Phe-D-Met-OMe, C24H36N4O7S.2H2O and tert-butoxycarbonyl-glycy-glycl-phenylalanine-norleucine methyl ester dihydrate, Boc-Gly-Gly-D-Phe-L-Nle-OMe, C25H38N4O7.2H2O, are described. The three molecules have the same conformation of the Boc-Gly Gly Phe-X-OMe tetrapeptide chain and display the same packing, consisting of couples of molecules linked head-to-tail by two hydrogen (N-HO) bonds; other hydrogen bonds, also involving two water molecules of crystallization, link these couples together, and give rise to a planar structure

Functional poly(2-oxazoline)s by direct amidation of methyl ester side chains

Poly(2-alkyl/aryl-2-oxazoline)s (PAOx) are biocompatible pseudopolypeptides that have received significant interest for biomedical applications in recent years. The growing popularity of PAOx in recent years is driven by its much higher chemical versatility compared with the gold standard in this field, poly(ethylene glycol) (PEG), while having similar beneficial properties, such as stealth behavior and biocompatibility. We further expand the PAOx chemical toolbox by demonstrating a novel straightforward and highly versatile postpolymerization modification platform for the introduction of side-chain functionalities. PAOx having side chain methyl ester functionalities is demonstrated to undergo facile uncatalyzed amidation reactions with a wide range of amines, yielding the corresponding PAOx with side-chain secondary amide groups containing short aliphatic linkers as well as a range of side-chain functionalities including acid, amine, alcohol, hydrazide, and propargyl groups. The PAOx with side-chain methyl ester groups can be prepared by either partial hydrolysis of a PAOx followed by the introduction of the methyl ester via modification of the secondary amine groups with methyl succinyl chloride or by the direct copolymerization of a nonfunctional 2-oxazoline monomer with a 2-methoxycarbonylethyl-2-oxazoline. Thus, this novel synthetic platform enables direct access to a wide range of side-chain functionalities from the same methyl-ester-functionalized poly(2-oxazoline) scaffold

l-Leucine Methyl Ester: The Female-Produced Sex Pheromone of the Scarab Beetle, Phyllophaga lanceolata

The female-produced sex pheromone of the scarab beetle Phyllophaga lanceolata was identified as the methyl ester of an essential amino acid, l-leucine. During field testing, 239 male P. lanceolata were caught in traps baited with l-leucine methyl ester. l-Isoleucine and l-valine methyl esters, similar in structure to l-leucine methyl ester and previously identified as female-produced sex pheromone compounds employed by other Phyllophaga species, were also tested. Addition of l-valine or l-isoleucine methyl esters to the l-leucine methyl ester in 1:1 ratios completely inhibited attraction of P. lanceolata males. Males of P. squamipilosa were also captured using l-leucine methyl ester. This is the first record of P. squamipilosa from Kansa

Experimental Evidence for Three Pheromone Races of the Scarab Beetle Phyllophaga anxia (LeConte)

This study offers experimental evidence for the existence of three pheromone races of the northern genitalic form of Phyllophaga anxia: one race in which females produce and males respond mainly to l-valine methyl ester, a second producing and responding to l-isoleucine methyl ester, and a third producing and responding to an intermediate range of blends of the two compounds. At Franklinville, NY, pheromone gland contents of females were analyzed using coupled gas chromatography-electroantennogram detection. Two types of females were found, one that produced greater than 99% l-valine methyl ester and another that produced greater than 99% l-isoleucine methyl ester. Capture-mark-release-recapture field tests with males at Franklinville established that most males were recaptured in traps baited with the same blends with which they were originally captured. The populations characterized at Franklinville, NY, have also been found at numerous locations from eastern Canada and the northeast and north central USA, sometimes in allopatry and sometimes in sympatry. At a site in Carver, MA, P. anxia males responded to blends of the methyl esters of l-valine and l-isoleucine, and Carver females produced blends similar to those to which the males responded. Populations responding to blends have been identified only from southeastern Massachusetts and Rhode Island. At a field site near Waterloo, NY, the addition of small proportions of l-isoleucine methyl ester to lures containing l-valine methyl ester did not affect trap captures, but higher proportions of l-isoleucine methyl ester were inhibitory, decreasing trap capture

UPLC-MS/MS analysis of ochratoxin A metabolites produced by Caco-2 and HepG2 cells in a co-culture system

Ochatoxin A (OTA) is one of the most important mycotoxins based on its toxicity. The oral route is the main gateway of entry of OTA into the human body, and specialized epithelial cells constitute the first barrier. The present study investigated the in vitro cytotoxic effect of OTA (5, 15 and 45 μM) and production of OTA metabolities in Caco-2 and HepG2 cells using a co-culture Transwell System to mimic the passage through the intestinal epithelium and hepatic metabolism. The results derived from MTS cell viability assays and transepithelial electrical resistance measurements showed that OTA was slightly cytotoxic at the lowest concentration at 3 h, but significant toxicity was observed at all concentrations at 24 h. OTA metabolites generated in this co-culture were ochratoxin B (OTB), OTA methyl ester, OTA ethyl ester and the OTA glutathione conjugate (OTA-GSH). OTA methyl ester was the major metabolite found in both Caco-2 and HepG2 cells after all treatments. Our results showed that OTA can cause cell damage through several mechanisms and that the OTA exposure time is more important that the dosage in in vitro studies. OTA methyl ester is proposed as an OTA exposure biomarker, although future studies should be conducted.The authors are grateful to the Spanish (Project AGL2011-24862) and Catalonian (XaRTA-Reference Network on Food Technology) Governments for their financial support. C.A. González-Arias thanks the Secretaria de Universitats i Recerca del Departament de Economia i Coneixement of the Generalitat de Catalunya for the pre-doctoral grant

Synthesis and structural characterization of 6-(N-Methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester isomers

A series of monoamide isomers have been successfully synthesised and characterised using combination of common spectroscopic techniques such Fourier Transform Infrared (FT-IR), 1H and 13C Nuclear Magnetic Resonance (NMR) and Ultraviolet-visible (UV-vis). The monoamide compounds namely 6-(3-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L1), 6-(4-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L2), 6-(5-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L3) and 6-(6-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L4) were prepared from reaction between 6-(methoxycarbonyl)pyridine-2-carboxylic acid with 2-amino-N-methylpyridine (where N = 3, 4, 5 and 6) by using acyl chloride reaction. In this present studies, the synthesis and characterization of these compounds are discussed along with the inductive effects contributed by methyl substituted groups at the pyridine ring

Evaluation of the Effect of Tocopherols on the Stability of Biodiesel

End of Project ReportA comprehensive study was carried out on the effects of naturally occurring tocopherols and carotenoids on the stability of biodiesel-grade methyl esters. Commercially available tocopherols and carotenoids, α-, γ- and δ-tocopherol, carotene and asthaxanthin, were added to destabilised methyl esters and the solutions were exposed to air at 65oC. The stabilising effect of the added tocopherols and carotenoids was determined from the number of days needed to reach the same increase of viscosity as destabilised methyl ester without tocopherols after 1 day. All three tocopherols stabilised methyl esters; γ- being the most effective and α- the least. The stabilising effect of tocopherols increased with concentration up to an optimum level. Concentrations above this level did not improve stability significantly. The stabilising effect of the tocopherols also depended on the composition of the methyl ester; they were most effective in tallow methyl ester, and had the least effect on sunflower methyl ester. Carotene and asthaxanthin had no effect on the stability of the methyl esters. However an unidentified carotenoid in rape methyl ester changed the oxidation pattern by reducing rates of peroxide and viscosity increase, without affecting overall stability

New dienol phytoalexins isolated from Arachis hypogaea leaves infected with Puccinia arachidis Speg.

Two dienol phytoalexins, 9-hydroxy-10,12-octadecadienoic methyl ester and 13-hydroxy-9,11-octadecadienoic methyl ester were isolated from groundnut leaves infected by P. arachidis. Extraction, purification, characterization and antifungal activity of these compounds are described and their possible role in host defences against pathogenic infections is discusse

Pembuatan Biodiesel dari Minyak Kelapa Menggunakan Microwave : Penggunaan Katalis KOH dengan Konsentrasi Rendah

Penelitian pembuatan methyl ester (biodiesel) dari minyak kelapa dengan katalis KOH dengan bantuan gelombang mikro (microwave) di latar belakangi oleh adanya krisis energi sehingga memerlukan metode baru untuk membuat renewable energy dalam hal ini adalah biodiesel. Tujuan dari penelitian ini adalah mempelajari proses pembuatan biodiesel dengan metode radiasi microwave, pengaruh konsentrasi katalis KOH, pengaruh daya, waktu pemanasan yang digunakan terhadap yield dan viskositas biodiesel yang dihasilkan. Pembuatan methyl ester (biodiesel) dari minyak kelapa dilakukan dengan perbandingan mol minyak : metanol = 1 : 9. Biodiesel yang dihasilkan kemudian dianalisa dengan uji viskositas, uji flash point, dan uji gas chromatography (GC). Yield optimum pada pembuatan methyl ester dari minyak kelapa dengan metode microwave-assisted transesterification untuk katalis KOH adalah konsentrasi 0,5% dengan daya 400 watt dan waktu reaksi 4 menit