Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid

Chirality ◽  
2011 ◽  
Vol 24 (2) ◽  
pp. 129-136 ◽  
Author(s):  
Selahattin Bozkurt ◽  
Mustafa Yilmaz ◽  
Abdulkadir Sirit
Keyword(s):  
Amino Acid ◽  
Amino Alcohol ◽  
Mandelic Acid ◽  
Membrane Carriers ◽  
Amino Acid Methylesters

Chiral calix[4]arenes bearing aminonaphthol moieties as membrane carriers for amino acid methyl esters and mandelic acid

2011 ◽  
Vol 22 (7) ◽  
pp. 791-796 ◽  
Author(s):  
Mustafa Durmaz ◽  
Selahattin Bozkurt ◽  
Hayriye Nevin Naziroglu ◽  
Mustafa Yilmaz ◽  
Abdulkadir Sirit
Keyword(s):  
Amino Acid ◽  
Mandelic Acid ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Membrane Carriers ◽  
Amino Acid Methyl Esters

Synthesis and application of L-N-Boc-N-methyl-β-hydroxyvaline in the preparation of a depsipeptide

2005 ◽  
Vol 83 (6-7) ◽  
pp. 793-800 ◽  
Author(s):  
James E Dettwiler ◽  
Laurent Bélec ◽  
William D Lubell
Keyword(s):  
Free Radical ◽  
Amino Acid ◽  
Methyl Ester ◽  
Hydrochloric Acid ◽  
Selective Oxidation ◽  
Building Block ◽  
Amino Alcohol ◽  
Tertiary Alcohol ◽  
Anhydrous Dioxane ◽  
Acidic Conditions

Enantiopure (>99% ee) L-N-tert-butyloxycarbonyl-N-methyl-β-hydroxyvaline (2) was synthesized in six steps and 43% overall yield from D-serine methyl ester (5). Methyl (4S)-N-(9-phenylfluoren-9-yl)-oxazolidine-4-carboxylate (7) was prepared in two steps and 73% yield by N-phenylfluorenation of 5 followed by cyclization of N-(PhF)amino alcohol 6 with formaldehyde and catalytic p-toluenesulfonic acid (PhF = 9-phenylfluoren-9-yl). The addition of MeLi to oxazolidine carboxylate 7 produced the tertiary alcohol 8 in 91% yield. Oxazolidines 8 equilibrated with oxazolidine 9 under acidic conditions. Reduction of pure 8 or the mixture of oxazolidines 8 and 9 with NaCNBH3 and hydrochloric acid in anhydrous dioxane afforded N-methyl amino diol 11 in 86%–92% yields. Attempts to selectively oxidize N-(PhF)amino diol 11 were unsuccessful; however, hydrogenation of 11 in the presence of di-tert-butyl dicarbonate gave the corresponding N-(Boc)amino diol 12 in 82% yield. Selective oxidation of diol 12 was performed using a cocktail containing TEMPO free radical, NaClO2, and NaOCl to give L-N-Boc-N-methyl-β-hydroxyvaline (2) in 87% yield. Coupling of β-hydroxyvaline 2 and (S)-2-hydroxy-3-methylbutanoate (15) was accomplished by using the methodology of Mitsunobu to provide depsipeptide Boc-(S)-HOMeVal-(R)-Hmb (4) for use as a building block in the synthesis of the cyclic antifungal depsipeptide aureobasidin B.Key words: N-methylated amino acid, serine, depsipeptide, aureobasidin.

Permeability of liposomes towards amino alcohol and amino acid nitroxides

1983 ◽  
Vol 33 (4) ◽  
pp. 303-312 ◽  
Author(s):  
D. Cantenys ◽  
C. Dogounkoff ◽  
M. Massol
Keyword(s):  
Amino Acid ◽  
Amino Alcohol

scholarly journals Benchmarking a new segmented K-band chirped-pulse microwave spectrometer and its application to the conformationally rich amino alcohol isoleucinol

2020 ◽  
Vol 22 (30) ◽  
pp. 17042-17051
Author(s):  
Mariyam Fatima ◽  
Cristóbal Pérez ◽  
Benjamin E. Arenas ◽  
Melanie Schnell ◽  
Amanda L. Steber
Keyword(s):  
Amino Acid ◽  
Amino Alcohol ◽  
Microwave Spectroscopy ◽  
Chirped Pulse ◽  
Pulse Microwave ◽  
Microwave Spectrometer ◽  
Potential Precursor ◽  
K Band

Isoleucinol, a potential precursor to the essential α-amino acid isoleucine, has been studied using microwave spectroscopy from 2–26 GHz, with the measurements between 18–26 GHz taking place on a newly designed spectrometer.

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