scholarly journals Synthesis and applications of secondary amine derivatives of (+)-dehydroabietylamine in chiral molecular recognition

2015 ◽  
Vol 13 (42) ◽  
pp. 10548-10555 ◽  
Author(s):  
Tiina Laaksonen ◽  
Sami Heikkinen ◽  
Kristiina Wähälä

(+)-Dehydroabietylamine (1a), the novel derivatives (2a–6a) and their NTf2 salts (1b–6b) were tested as chiral NMR solvating agents for the resolution of enantiomers of Mosher's acid and other carboxylic acids, and their n-Bu4N salts.

1993 ◽  
Vol 46 (3) ◽  
pp. 315 ◽  
Author(s):  
WM Johnson ◽  
SW Littler ◽  
CE Skene

Several derivatives of the novel 1,4,2-oxathiazin-6(5H)-one system were prepared by reaction of mercapto carboxylic acids with substituted carbohydroximoyl chlorides and subsequent cyclization of the resulting oxime acid with dicyclohexylcarbodiimide . The stability of the 1,4,2-oxathiazin-6(5H)-one system to acid and base conditions as well as to various nucleophiles was investigated.


2005 ◽  
Vol 70 (12) ◽  
pp. 2066-2074 ◽  
Author(s):  
Šárka Chalupová ◽  
Antonín Holý ◽  
Milena Masojídková

We have studied the reaction of 1-[2-(phosphonomethoxy)ethyl]cytosine (1) and its diisopropyl ester (2) with triethylammonium hydrogensulfite in 60% aqueous methanol. In the presence of some primary or secondary amine salts, at 25-70 °C, this reaction affords transaminated derivatives 4a-4e and 5a, 5b as main products accompanied by uracil compounds. However, with certain amines the reaction failed.


2005 ◽  
Vol 60 (4) ◽  
pp. 471-475 ◽  
Author(s):  
Barbara Orzeszko ◽  
Tomasz Świtaj ◽  
Anna B. Jakubowska-Mućka ◽  
Witold Lasek ◽  
Andrzej Orzeszko ◽  
...  

Certain adamantylated heterocycles were previously shown to enhance the secretion of tumor necrosis factor alpha (TNF-α) by murine melanoma cells that have been transduced with the gene for human TNF-α and constitutively expressed this cytokine. The stimulatory potency of those compounds depended, among other factors, on the structure of the linker between the adamantyl residue and the heterocyclic core. In the present study, a series of (1-adamantyl)alkylsulfanyl derivatives of heterocyclic compounds was prepared by alkylation of the corresponding thioheterocyles. Of the novel adamantylalkylthio compounds tested in the aforementioned cell line, 2-(2-adamantan-1-ylethylsulfanyl)- 4-methyl-pyrimidine was found to be the most active


1975 ◽  
Vol 28 (6) ◽  
pp. 1249 ◽  
Author(s):  
SE Livingstone ◽  
N Saha

The nickel(II), palladium(II), platinum(II), copper(II), zinc(II) and rhodium(III) chelates of the new fluorinated monothio-β-diketones RC(SH)=CHCOCF3 (R = Pri, Bui) and the iron(III), ruthenium(III) and cobalt(III) chelates of PriC(SH)=CHCOCF3 have been prepared. The mass spectra of all but the two copper chelates have been obtained. The novel features of the spectra are the occurrence of the ions M-(R-H), M-R, and M-LH and the loss of H2S from the ions M-LH and M-L.


2014 ◽  
Vol 10 ◽  
pp. 1354-1364 ◽  
Author(s):  
Melanie Rauschenberg ◽  
Eva-Corrina Fritz ◽  
Christian Schulz ◽  
Tobias Kaufmann ◽  
Bart Jan Ravoo

The molecular recognition of carbohydrates and proteins mediates a wide range of physiological processes and the development of synthetic carbohydrate receptors (“synthetic lectins”) constitutes a key advance in biomedical technology. In this article we report a synthetic lectin that selectively binds to carbohydrates immobilized in a molecular monolayer. Inspired by our previous work, we prepared a fluorescently labeled synthetic lectin consisting of a cyclic dimer of the tripeptide Cys-His-Cys, which forms spontaneously by air oxidation of the monomer. Amine-tethered derivatives of N-acetylneuraminic acid (NANA), β-D-galactose, β-D-glucose and α-D-mannose were microcontact printed on epoxide-terminated self-assembled monolayers. Successive prints resulted in simple microarrays of two carbohydrates. The selectivity of the synthetic lectin was investigated by incubation on the immobilized carbohydrates. Selective binding of the synthetic lectin to immobilized NANA and β-D-galactose was observed by fluorescence microscopy. The selectivity and affinity of the synthetic lectin was screened in competition experiments. In addition, the carbohydrate binding of the synthetic lectin was compared with the carbohydrate binding of the lectins concanavalin A and peanut agglutinin. It was found that the printed carbohydrates retain their characteristic selectivity towards the synthetic and natural lectins and that the recognition of synthetic and natural lectins is strictly orthogonal.


ChemInform ◽  
2014 ◽  
Vol 45 (44) ◽  
pp. no-no
Author(s):  
A. S. Tikhomirov ◽  
A. E. Shchekotikhin ◽  
Yu. N. Luzikov ◽  
A. M. Korolev ◽  
M. N. Preobrazhenskaya

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