The 4-(methylthio)phenyl ester for the synthesis of polypeptides of a known repeating sequence of amino acids. Synthesis of poly-(L-lysylglycyl)glycine 1-C14 ethyl ester hydrobromide

1970 ◽  
Vol 48 (16) ◽  
pp. 2509-2511 ◽  
Author(s):  
Brian J. Johnson ◽  
Donna S. Rea
Keyword(s):  
Amino Acids ◽  
Ethyl Ester ◽  
Title Compound ◽  
Ester Hydrochloride ◽  
Phenyl Ester ◽  
Protecting Group ◽  
High Dilution ◽  
Protective Groups ◽  
Protected Tetrapeptide

The synthesis of the tetrapeptide, N-t-butoxycarbonyl-ε-N-carbobenzoxy-L-lysylglycyl-ε-N-carbobenzoxy-L-lysylglycine 4-(methylthio)phenyl ester is described. The utility of this protective ester is shown by its easy conversion to the protected tetrapeptide 4-(methylsulfonyl)phenyl activated ester without decomposition. Removal of the N-butoxycarbonyl protecting group afforded the polymerizing unit, ε-N-carbobenzoxy-L-lysylglycyl-ε-N-carbobenzoxy-L-lysylglycine 4-(methylsulfonyl)phenyl ester. Polymerization of this material on the partially blocked monomer glycine-1-C14 ethyl ester hydrochloride, at a relatively high dilution, gave poly-(ε-N-carbobenzoxyl-L-lysylglycyl)glycine-1-C14 ethyl ester. The carbobenzoxy protective groups were removed to give the title compound.

SYNTHESIS OF A NEW α-AMINO ACID, S-METHYL-β,β-DIMETHYLCYSTEINE

1946 ◽  
Vol 24b (1) ◽  
pp. 28-36 ◽  
Author(s):  
Kenneth Savard ◽  
Edwin M. Richardson ◽  
Gordon A. Grant
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Ester ◽  
Ethyl Ester ◽  
Ester Hydrochloride ◽  
First Time

A new sulphur-containing α-amino acid, S-methyl-β,β-dimethylcysteine has been prepared from S-benzyl-β,β-dimethylcysteine. These two compounds and the intermediate β,β-dimethylcysteine may be of physiological importance.S-Benzyl-β,β-dimethylcysteine has been prepared by the addition of benzyl mercaptan to α-benzoylamino-β,β-dimethylacrylic acid, its azlactone, and methyl ester, followed by hydrolysis.In addition to the above three new sulphur-containing α-amino acids, the following compounds are described, as far as the authors are aware, for the first time: methyl α-benzoylamino-β,β-dimethylacrylate, S-benzyl-N-benzoyl-β,β-dimethylcysteine and its methyl ester, the hydantoin of S-benzyl-β,β-dimethylcysteine, and S-benzyl-β,β-dimethylcysteine ethyl ester hydrochloride, and helianthate.

Synthesis of (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(Carboxymethyl)]oxime, New Hapten for Dihydrotestosterone (17β-hydroxy-5α-androstan-3-one)

1997 ◽  
Vol 62 (10) ◽  
pp. 1642-1649 ◽  
Author(s):  
Ivan Černý ◽  
Tereza Slavíková ◽  
Vladimír Pouzar
Keyword(s):  
Hydroxy Group ◽  
Carboxy Group ◽  
Title Compound ◽  
Oxidative Cleavage ◽  
Hydroxy Derivative ◽  
Borohydride Reduction ◽  
Protecting Group ◽  
Free Hydroxy Group

Addition of 4-methoxybenzyl alcohol to 3β-hydroxy-5α-androst-15-en-17-one gave the mixture of isomeric 15-(4-methoxyphenyl)methoxy derivatives from which, after acetylation and chromatography, the major 15β isomer was separated. Borohydride reduction gave 17β-hydroxy derivative which was protected as methoxymethyl ether. Oxidative cleavage of protecting group at position 15 and the subsequent Jones oxidation afforded corresponding 15-ketone. Its oximation with O-(carboxymethyl)hydroxylamine, deacetylation and methylation with diazomethane gave protected O-(carboxymethyl)oxime derivative with free hydroxy group at position 3. Its oxidation afforded dihydrotestosterone derivative and successive deprotection of position 17 and of carboxy group led to final (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(carboxymethyl)]oxime. The title compound was designed as dihydrotestosterone hapten for heterologous radioimmunoassays.

Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues

2016 ◽  
Vol 14 (44) ◽  
pp. 10473-10480 ◽  
Author(s):  
Sylvain Daunay ◽  
Remi Lebel ◽  
Laurence Farescour ◽  
Jean-Claude Yadan ◽  
Irene Erdelmeier
Keyword(s):  
Amino Acids ◽  
Protecting Group ◽  
One Pot ◽  
Step Procedure ◽  
Sulfur Containing

Natural and novel sulfur-containing amino acids are preparedviaa new regioselective one-pot two-step procedure.

Enzymatic resolution of (±)-5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester and its transformations into polyfunctionalised amino acids and dipeptides

2009 ◽  
Vol 20 (16) ◽  
pp. 1940-1947 ◽  
Author(s):  
Giuseppe Cremonesi ◽  
Piero Dalla Croce ◽  
Alessandra Forni ◽  
Maddalena Gallanti ◽  
Raffaella Gandolfi ◽  
...  
Keyword(s):  
Amino Acids ◽  
Carboxylic Acid ◽  
Ethyl Ester ◽  
Acid Ethyl Ester ◽  
Enzymatic Resolution

2,5-Dimethylphenacyl carbamate: a photoremovable protecting group for amines and amino acids

2007 ◽  
Vol 6 (1) ◽  
pp. 50-56 ◽  
Author(s):  
Laxminarayana Kammari ◽  
Lukáš Plíštil ◽  
Jakob Wirz ◽  
Petr Klán
Keyword(s):  
Amino Acids ◽  
Protecting Group

scholarly journals Monitoring of Irinotecan in Human Plasma: Sensitive Fluorescent Nanogels by Molecular Imprinting

2019 ◽  
Author(s):  
Martina Tommasini ◽  
Elena Pellizzoni ◽  
Valentina Iacuzzi ◽  
Elena Marangon ◽  
Paola Posocco ◽  
...  
Keyword(s):  
Amino Acids ◽  
Fluorescence Quenching ◽  
Human Plasma ◽  
Molecular Imprinting ◽  
Plasma Sample ◽  
Direct Detection ◽  
Fluorescent Nanoparticles ◽  
High Dilution ◽  
Molecularly Imprinted

A series of fluorescent molecularly imprinted nanogels to detect irinotecan (CPT11) were prepared and characterized. A set of amino acids and napthalimide polymerisable derivatives allowed to obtain polymers as soluble fluorescent nanoparticles by high dilution imprinted synthesis. The direct detection of irinotecan in human plasma was obtained by fluorescence quenching of the naphtalimide-based imprinted materials. The plasma sample treated with acetonitrile allowed the detection of irinotecan in the 10nM – 30μM range. The LOD was 9.4 nM, with within-run variability 10% and day to day variability 13%.<br>

Iron-Catalyzed Cyclopropanation with Glycine Ethyl Ester Hydrochloride in Water

2012 ◽  
Vol 14 (8) ◽  
pp. 2162-2163 ◽  
Author(s):  
Bill Morandi ◽  
Amund Dolva ◽  
E. M. Carreira
Keyword(s):  
Ethyl Ester ◽  
Ester Hydrochloride ◽  
Glycine Ethyl Ester
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