Chiral recognition of amino-acid esters by a glucose-derived macrocyclic receptor

2021 ◽  
Author(s):  
Pit Dominique ◽  
Martin Schnurr ◽  
Bartosz Lewandowski

We report a glucose-based crown ether capable of chiral recognition of a wide range of amino-acid methyl esters in aqueous environment. The enantioselectivities towards amino-acids with extended hydrophobic side chains...


2019 ◽  
Vol 17 (11) ◽  
pp. 3040-3047
Author(s):  
Jia-Yun Haung ◽  
Indrajeet J. Barve ◽  
Chung-Ming Sun

A one-pot multicomponent reaction for assembling substituted 4-arylidene imidazolin-5-ones from l-amino acid methyl esters, iso-, isothio- or isoselenocyanates, and α-bromoketones has been discovered.



Parasitology ◽  
1988 ◽  
Vol 96 (2) ◽  
pp. 289-296 ◽  
Author(s):  
M. Rabinovitch ◽  
V. Zilberfarb

SummaryL-amino acid esters such as leucine methyl ester (Leu-OMe) destroy Leishmania mexicana amazonensis amastigotes by a mechanism which may involve hydrolysis of the compounds by parasite enzymes. Moreover, several esters (e.g. Ile-OMe) prevent the killing of parasites by Leu-OMe, perhaps by inhibition of the hydrolytic enzymes. We show here that certain amino acid amides are also leishmanicidal. Killing of Leishmania within macrophages was assessed microscopically, and that of isolated amastigotes was measured by reduction of the tetrazolium MTT. Amino acid amides were generally less active than the methyl esters and several were more toxic to the macrophages, as determined by inspection of Giemsa-stained preparations. Ranks of activity of the amides on isolated amastigotes were Trp > Leu > Phe > Met > Tyr. The amides of Ala, Gly, Val, Ile, His and D-Leu were inactive. This pattern of activity is similar to that of amino acid methyl esters. Ile-NH2 and a few other amides protected intracellular as well as isolated parasites from killing by Leu-OMe. Conversely, Ile-OMe reduced the toxicity of Leu-NH2 for isolated amastigotes. None of the esters or amides assayed prevented the destruction of Leishmania by Trp-NH2. The results are compatible with the view that amino acid esters and amides may be recognized by the same or similar parasite enzymes.



RSC Advances ◽  
2015 ◽  
Vol 5 (95) ◽  
pp. 77538-77544 ◽  
Author(s):  
Arukali Sammaiah ◽  
Korlipara V. Padmaja ◽  
Shiva Shanker Kaki ◽  
Rachapudi B. N. Prasad

Novel multifunctional additives were synthesized from methyl oleate via thioglycolic acid addition followed by condensation with different amino acid methyl esters.





1971 ◽  
Vol 26 (8) ◽  
pp. 762-764 ◽  
Author(s):  
I. Z. Siemion ◽  
L. Wilschowitz

The racemization rate of N- [p-nitrobenzylidene] -α-amino acid esters was found to be even thousand-fold smaller than that of the azlactones of N-acyl-α-amino acids. t-Butyl esters of N-[p- nitrobenzylidene]-α-amino acids are much more stable to racemization as the correspondent methyl esters.





Sign in / Sign up

Export Citation Format

Share Document