ChemInform Abstract: Thioacylation of the Amino Group of an Amino Acid

ChemInform ◽  
2000 ◽  
Vol 31 (40) ◽  
pp. no-no
Author(s):  
Graham C. Barrett
Keyword(s):  
Amino Acid ◽  
Amino Group

Ligand-free CuI-catalyzed selective C–N coupling of aliphatic amino group of α-amino acid amides with ortho-dihaloarenes

2013 ◽  
Vol 54 (45) ◽  
pp. 6045-6048 ◽  
Author(s):  
Yan Wang ◽  
Xingzhao Tu ◽  
Xirui Lv ◽  
Lihong Zhou ◽  
Qingle Zeng
Keyword(s):  
Amino Acid ◽  
Amino Group ◽  
Ligand Free

Effect of amino group protonation on the carboxyl group in aqueous glycine observed by O 1s X-ray emission spectroscopy

2018 ◽  
Vol 20 (36) ◽  
pp. 23214-23221 ◽  
Author(s):  
Y. Horikawa ◽  
T. Tokushima ◽  
O. Takahashi ◽  
Y. Harada ◽  
A. Hiraya ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Amino Acid ◽  
Electronic Structures ◽  
Emission Spectroscopy ◽  
Selective Excitation ◽  
Carboxyl Group ◽  
Amino Group ◽  
X Ray ◽  
Excitation Conditions ◽  
Amino Acid Glycine

The valence electronic structures of the amino acid glycine in aqueous solution were investigated in detail through X-ray emission spectroscopy at O 1s excitation under selective excitation conditions of the CO site in the carboxyl group.

Amino Acid Salt Catalyzed Asymmetric Addition Reaction of Acetylacetone to Maleimides and 2-(2-Oxoindolin-3-ylidene)malononitriles

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1241-1245 ◽  
Author(s):  
Haiyan Wu ◽  
Hongxin Liu ◽  
Juan Li ◽  
Xinhua Li ◽  
Hong-Ping Xiao ◽  
...  
Keyword(s):  
Amino Acid ◽  
Addition Reaction ◽  
Optical Purity ◽  
Activation Mechanism ◽  
Amino Group ◽  
Acid Salt ◽  
Natural Amino Acid ◽  
Catalytic Potential ◽  
Amino Acid Salt ◽  
Secondary Amino

The exploration of catalytic potential of natural amino acid salt in activation of 1,3-dicarbonyls was carried out, in which maleimides and 2-(2-oxoindolin-3-ylidene)malononitriles were found to be good electrophiles and afforded the desired products with excellent yield and moderate optical purity. Control experiments showed that the secondary amino group of barium (S)-prolinate is critical to the catalytic activity as well as enantiocontrol, thus revealed an enamine activation mechanism is possible in the present methodology.

N-DICHLOROACETYL DERIVATIVES OF SERINE AND THREONINE AND OF THEIR ESTERS AND SODIUM SALTS

1960 ◽  
Vol 38 (7) ◽  
pp. 1135-1140 ◽  
Author(s):  
I. Levi ◽  
A. E. Koller ◽  
G. Laflamme ◽  
J. W. R. Weed
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Antitumor Activity ◽  
Amino Acid Ester ◽  
Amino Group ◽  
Sodium Salts ◽  
Sarcoma 37 ◽  
Walker Carcinoma ◽  
Derivatives Of ◽  
Dichloroacetyl Chloride

The N-dichloroacetyl derivatives of DL-serine and DL-threonine were prepared by the Schotten–Baumann reaction from the amino acids and dichloroacetyl chloride. Negative ninhydrin tests coupled with elementary analyses indicated that only the amino group was acylated. The ester derivatives of these compounds were prepared either by esterification of the N-dichloroacetyl-DL-amino acid with diazomethane or by the reaction of the amino acid ester with dichloroacetyl chloride in the presence of triethylamine. The sodium salts and the esters were tested for antitumor activity against sarcoma 37 in mice and Walker carcinoma 256 in rats. In both cases regression of the tumors was obtained.

Intestinal Absorption of Amino Acid Derivatives: Importance of the Free a-Amino Group

1982 ◽  
Vol 71 (10) ◽  
pp. 1138-1141 ◽  
Author(s):  
G.L. Amidon ◽  
M. Chang ◽  
D. Fleisher ◽  
R. Allen
Keyword(s):  
Amino Acid ◽  
Intestinal Absorption ◽  
Amino Acid Derivatives ◽  
Amino Group

Transformation of the Carboxyl Group of an Amino Acid to Variously Substituted Imidazoles through a Davidson-Type Heterocyclization

Synthesis ◽  
2019 ◽  
Vol 51 (09) ◽  
pp. 1961-1968 ◽  
Author(s):  
Jim Küppers ◽  
Michaela Hympánová ◽  
Tim Keuler ◽  
Andreas Schneider ◽  
Gregor Schnakenburg ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Amino Acids ◽  
Amino Acid ◽  
Carboxylic Acid ◽  
Building Blocks ◽  
Carboxyl Group ◽  
Amino Group ◽  
Combinatorial Approach ◽  
X Ray ◽  
Imidazole Derivatives

The modification of amino acids leads to valuable building blocks for the synthesis of bioactive compounds. By keeping the amino group protected, the carboxylic acid functionality can be converted in two steps into an imidazole moiety via a Davidson-like heterocyclization. This reaction allows for a combinatorial approach, in which two positions at the heterocycle can be modified. Herein, we report the synthesis of such imidazole derivatives by employing N-protected cyclohexylalanine as the starting material. Different α-halo ketones were used and two points of diversity, positions 4 and 5, were examined. The structure of the final imidazole derivatives was confirmed by three X-ray crystal structure analyses and their protease inhibiting activities were evaluated.

Synthesis of Peptide Mimetics and Amino Acid Mimetics Bearing Aminoxy Instead of Amino Group

2001 ◽  
pp. 608-609
Author(s):  
Toratane Munegumi ◽  
Tokanori Yoshii ◽  
Masahide Nakamura ◽  
Kunie Sakurai
Keyword(s):  
Amino Acid ◽  
Peptide Mimetics ◽  
Amino Group

scholarly journals Enzyme-assisted semisynthesis of polypeptide active esters and their use

1988 ◽  
Vol 249 (1) ◽  
pp. 83-88 ◽  
Author(s):  
K Rose ◽  
C Herrero ◽  
A E I Proudfoot ◽  
R E Offord ◽  
C J A Wallace
Keyword(s):  
Amino Acid ◽  
Cytochrome C ◽  
Amino Acid Ester ◽  
Amino Group ◽  
Horse Heart Cytochrome ◽  
C Terminus ◽  
Active Ester ◽  
Chemical Coupling ◽  
Concentrated Solution ◽  
Horse Heart Cytochrome C

A method is described for the preparation of polypeptides activated uniquely at the C-terminus. The polypeptide is incubated in a concentrated solution of an amino acid active ester, the latter having its amino group free but adequately protected by protonation. The amino acid ester is coupled via its amino group to the C-terminus of the polypeptide by enzymic catalysis (reverse proteolysis). The resulting polypeptide C-terminal active ester is then isolated and coupled to a suitable amino component (generally a polypeptide) in a subsequent chemical coupling. The method appears to be generally applicable; fragments of horse heart cytochrome c, and porcine insulin, are used as examples. Two new analogues of cytochrome c have been prepared by using this method, with yields of up to 60% in the final coupling. Scope and limitations of the method are discussed.

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