Synthesis of enantiomers of N-(2-aminopurin-6-yl)amino acids

Краснов, В. П.; Vigorov, A. Yu.; Gruzdev, Dmitry А.; Левит, Г. Л.; Demin, A. M.; Низова, И. А.; Тумашов, А. А.; Садретдинова, Л. Ш.; Gorbunov, Evgeny B.; Charushin, Valery N.

doi:10.1007/s11172-015-1125-x

Cited by 10 publications

(2 citation statements)

References 36 publications

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“…Establishment of the structure of the adenylosuccinate ( Figure 1 ) involved in the purine nucleotide cycle prompted researchers to synthesize a series of purine bases substituted at C6 by chiral amino acid residues [ 6 , 7 , 8 , 9 ]. Conjugates were synthesized both with amino acids [ 10 , 11 ] and with corresponding methyl esters [ 10 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of 2-Chloropurine Arabinonucleosides with Chiral Amino Acid Amides at the C6 Position and an Evaluation of Antiproliferative Activity In Vitro

Eletskaya

Berzina

Fateev

et al. 2023

IJMS

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A number of purine arabinosides containing chiral amino acid amides at the C6 position of the purine were synthesized using a transglycosylation reaction with recombinant E. coli nucleoside phosphorylases. Arsenolysis of 2-chloropurine ribosides with chiral amino acid amides at C6 was used for the enzymatic synthesis, and the reaction equilibrium shifted towards the synthesis of arabinonucleosides. The synthesized nucleosides were shown to be resistant to the action of E. coli adenosine deaminase. The antiproliferative activity of the synthesized nucleosides was studied on human acute myeloid leukemia cell line U937. Among all the compounds, the serine derivative exhibited an activity level (IC50 = 16 μM) close to that of Nelarabine (IC50 = 3 μM) and was evaluated as active.

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Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of 2-Chloropurine Arabinonucleosides with Chiral Amino Acid Amides at the C6 Position and an Evaluation of Antiproliferative Activity In Vitro

Eletskaya

Berzina

Fateev

et al. 2023

IJMS

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“…Recently, we have synthesized a number of 6‐substituted derivatives of purine and 2‐aminopurine containing amino acids (Krasnov et al., , ; Vigorov et al., ) and heterocyclic amines (Eletskaya et al., ; Gruzdev, Musiyak, Chulakov, Levit, & Krasnov, ) fragments. Among them, compounds with high antimycobacterial were found (Krasnov et al., ).…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of novel purine nucleosides bearing a chiral benzoxazine fragment

et al. 2019

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A series of ribo‐ and deoxyribonucleosides bearing 2‐aminopurine as a nucleobase with 7,8‐difluoro‐ 3,4‐dihydro‐3‐methyl‐2H‐[1,4]benzoxazine (conjugated directly or through an aminohexanoyl spacer) was synthesized using an enzymatic transglycosylation reaction. Nucleosides 3‐6 were resistant to deamination under action of adenosine deaminase (ADA) Escherichia coli and ADA from calf intestine. The antiviral activity of the modified nucleosides was evaluated against herpes simplex virus type 1 (HSV‐1, strain L2). It has been shown that at sub‐toxic concentrations, nucleoside (S)‐4‐[2‐amino‐9‐(β‐D‐ribofuranosyl)‐purin‐6‐yl]‐7,8‐difluoro‐3,4‐dihydro‐3‐methyl‐2H‐[1,4]benzoxazine exhibit significant antiviral activity (SI > 32) on the model of HSV‐1 in vitro, including an acyclovir‐resistant virus strain (HSV‐1, strain L2/R).

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Analysis of racemic conjugates of purine with heterocyclic amines by chiral high-performance liquid chromatography

et al. 2018

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Synthesis of enantiomers of N-(2-aminopurin-6-yl)amino acids

Cited by 10 publications

References 36 publications

Enzymatic Synthesis of 2-Chloropurine Arabinonucleosides with Chiral Amino Acid Amides at the C6 Position and an Evaluation of Antiproliferative Activity In Vitro

Enzymatic Synthesis of 2-Chloropurine Arabinonucleosides with Chiral Amino Acid Amides at the C6 Position and an Evaluation of Antiproliferative Activity In Vitro

Enzymatic synthesis of novel purine nucleosides bearing a chiral benzoxazine fragment

Analysis of racemic conjugates of purine with heterocyclic amines by chiral high-performance liquid chromatography

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