scholarly journals 6-Oxyindan-1-ones with dipeptide chains

2019 ◽  
Vol 7 (2) ◽  
pp. 111-119
Author(s):  
Serhiy Shilin ◽  
Olga Shablykina ◽  
Igor Levkov ◽  
Oleksandra Bugera ◽  
Zoia Voitenko
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Amino Acid ◽  
Direct Interaction ◽  
Carboxyl Group ◽  
Amino Group ◽  
Hydroxysuccinimide Esters

Through N-acylation of a- or b-amino acid units by 2-(3-oxo-2,3-dihydro-1H-inden-5-yloxy)acetic acid using the method of N-hydroxysuccinimide esters new dipeptide indan-1-one derivatives were obtained. In general, the direct interaction of the acetic carboxyl group of the substrate with the amino group of the a- or b-dipeptide is a more productive strategy than the sequential peptidic condensation of the two amino acids.

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.

Specificity of the transport system for neutral amino acids in the hamster intestine

1962 ◽  
Vol 202 (5) ◽  
pp. 919-925 ◽  
Author(s):  
Edmund C. C. Lin ◽  
Hiroshi Hagihira ◽  
T. Hastings Wilson
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Transport System ◽  
Side Chain ◽  
Carboxyl Group ◽  
Amino Group ◽  
Methyl Group ◽  
Neutral Amino Acids ◽  
Active Transport System ◽  
Everted Sacs

The specificity of the active transport system for neutral amino acids has been studied with everted sacs of hamster intestine. Amino acids with modifications or replacements of the carboxyl, amino, or α-hydrogen groups were poorly transported and were poor inhibitors of the transport of other l-amino acids. The carboxyl group must remain free, the amino group must not be in the tertiary or quaternary state, and the α-hydrogen can not be replaced by a methyl group without serious effect on the transport rate. It was concluded that the l-amino acids were distinguished from the d-isomers by the interaction of the carrier with the carboxyl group, the amino group, and the α-hydrogen. The side chain of the amino acid must be nonpolar but there is relatively little restriction on its structure.

Succinimidyl esters of fatty acids for amino acid acylations

1976 ◽  
Vol 54 (5) ◽  
pp. 733-737 ◽  
Author(s):  
Alenka Paquet
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Amino Acid ◽  
Free Amino ◽  
Side Chain ◽  
Amino Acid Esters ◽  
Amino Group ◽  
Acyl Chlorides ◽  
Hydroxysuccinimide Esters ◽  
Acid Esters

Fatty acid N-hydroxysuccinimide esters have been prepared from the thallium(I) salt of N-hydroxysuccinimide and the corresponding acyl chlorides in essentially quantitative yields. These active esters were used for acylation of amino acid esters in organic solvents, or of free amino acids in aqueous medium. The title compounds were found to be selective towards the side chain amino group of lysine. An efficient preparation of ε-N-benzyloxycarbonyl-L-lysine using benzyl succinimidyl carbonate is described.

scholarly journals 6-Oxyindan-1-ones with amino acid fragments

2018 ◽  
Vol 6 (2) ◽  
pp. 18-26 ◽  
Author(s):  
Serhiy Shilin ◽  
Illya Lenko ◽  
Olga Shablykina ◽  
Volodymyr Khilya
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Amino Acid ◽  
Methyl Esters ◽  
Imidazole Derivatives ◽  
Acid Methyl ◽  
Hydroxysuccinimide Esters ◽  
Amino Acid Methyl Esters

New indan-1-one derivatives (8 examples) with amino acid fragments were synthesized through the N-acylation of the amino acids by 2-(3-oxo-2,3-dihydro-1H-inden-5-yloxy)acetic acid using the method of activated N-hydroxysuccinimide esters. To obtain corresponding methyl esters (2 examples) two ways were possible: the N-acylation of the amino acid methyl esters by 2-(3-oxo-2,3-dihydro-1-inden-5-yloxy)acetic acid through the activated imidazole derivatives or methylation of the carboxylic function of preformed N-{[(1-oxoindan-6-yl)oxy]acetyl}amino acids.

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 group requirement for in vitro intestinal transport of amino acids

1962 ◽  
Vol 202 (1) ◽  
pp. 171-173 ◽  
Author(s):  
Richard P. Spencer ◽  
Ted M. Bow ◽  
Mary Anne Markulis
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Cinnamic Acid ◽  
Concentration Gradient ◽  
Anthranilic Acid ◽  
Intestinal Transport ◽  
Amino Group ◽  
Phenylpyruvic Acid ◽  
Phenyllactic Acid

The amino group requirement for transintestinal transport of amino acids against a concentration gradient was investigated using hamster everted intestinal sacs. Although glycine (5 x 10–3 m) was transported against a concentration gradient, acetic acid was not. Similarly, l-phenylalanine was transported, whereas phenylpyruvic acid, phenylpropionic acid, phenyllactic acid, and cinnamic acid were not. l-Tryptophan was transported, but indolyllactic acid was not. The amino group was thus essential for transport by this system. n-Methylglycine and l-proline were accumulated from mucosa to serosa against a concentration gradient. Hence, one hydrogen of the amino group can be replaced. However, n-phenylglycine was not accumulated across these preparations, suggesting that the moiety replacing the amino hydrogen can not be sterically bulky. α-l-Alanine was transported against a concentration gradient from mucosa to serosa, but ß-alanine was not. This is in contrast to other systems which accumulate ß-alanine against a concentration gradient. Anthranilic acid, with the amino group in a relative ß position, was also not accumulated across everted intestinal sacs.

scholarly journals Synthesis of Chiral Thiourea-Thioxanthone Hybrids

Synthesis ◽  
2017 ◽  
Vol 49 (23) ◽  
pp. 5238-5250 ◽  
Author(s):  
Florian Mayr ◽  
Lisa-Marie Mohr ◽  
Elsa Rodriguez ◽  
Thorsten Bach
Keyword(s):  
Amino Acids ◽  
Phenyl Isothiocyanate ◽  
Carboxyl Group ◽  
Amino Group ◽  
Protecting Group

Four different 1-aminocyclohexanes bearing a tethered thioxanthone group in the 2-position were prepared. The synthesis commenced with the respective N-protected β-amino acids, the carboxyl group of which was employed for the introduction of the thioxanthone moiety. After construction of the thioxanthone and protecting group removal, the conversion of the amino group into the respective thiourea was accomplished by treatment with N-3,5-bis(trifluoromethyl)phenyl isothiocyanate and yielded the title compounds in which the thioxanthone resides in different spatial positions relative to the thiourea motif. Overall yields varied between 20–35%.

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.

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