Синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну
A synthetic approach has been developed for the preparation of new bioisosteres of homoproline, namely α-hydroxyphosphonic acids. At the key stages of the synthesis, the phosphorylation of carbonyl derivatives of (S)- and (R)-proline via the Abramov reaction was employed. The resulting α-hydroxyphos...
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Ukrainica Bioorganica Acta| _version_ | 1869381606535331840 |
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| author | Kolodiazhna, Anastasiia O. Prysiazhnuk, Dmytro V. Gryshkun, Yevgen V. |
| author_facet | Kolodiazhna, Anastasiia O. Prysiazhnuk, Dmytro V. Gryshkun, Yevgen V. |
| author_institution_txt_mv | [
{
"author": "Anastasiia O. Kolodiazhna",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Dmytro V. Prysiazhnuk",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Yevgen V. Gryshkun",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine"
}
] |
| author_sort | Kolodiazhna, Anastasiia O. |
| baseUrl_str | https://bioorganica.com.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-06-29T16:07:07Z |
| description | A synthetic approach has been developed for the preparation of new bioisosteres of homoproline, namely α-hydroxyphosphonic acids. At the key stages of the synthesis, the phosphorylation of carbonyl derivatives of (S)- and (R)-proline via the Abramov reaction was employed. The resulting α-hydroxyphosphonic acids are promising compounds with, potential biologicalactivity and may serve as valuable candidates for the development of new pharmaceuticals and physiologically active compounds  |
| doi_str_mv | 10.15407/bioorganica2025.02.053 |
| first_indexed | 2026-02-08T07:59:48Z |
| format | Article |
| fulltext |
ISSN 1814-9758. Ukr. Bioorg. Acta, 2025, Vol. 20, N 2
UDC 661.741+547.293/.294
DOI: https://doi.org/10.15407/bioorganica2025.02.053
53
RESEARCH ARTICLE
Synthesis of new α-hydroxyphosphonic acids – phosphorus analogues
of homoproline
Anastasiia O. Kolodiazhna*, Dmytro V. Prysiazhnuk, Yevgen V. Gryshkun
V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine
Abstract: A synthetic approach has been developed for the preparation of new bioisosteres of homoproline, namely α-hydroxyphosphonic
acids. At the key stages of the synthesis, the phosphorylation of carbonyl derivatives of (S)- and (R)-proline via the Abramov reaction was
employed. The resulting α-hydroxyphosphonic acids are promising compounds with potential biological activity and may serve as
valuable candidates for the development of new pharmaceuticals.
Keywords: α-hydroxyphosphonic acid; phosphorus analogs of amino acids; Abramov reaction; biological activity.
Introduction
Organophosphorus compounds, i.e., compounds
containing a C-P bond, are widely used in modern
medicine, agriculture, industry, and organic synthesis.
Organophosphorus compounds featuring a P-C bond were
first isolated from living organisms in 1959 [1, 2]. Shortly
thereafter, many related species were identified in hundreds
of aquatic and terrestrial animals and microorganisms [3].
α-Hydroxyphosphonic esters, regarded as an important class
of biologically active compounds, have attracted attention
due to their antibacterial, antiviral, antibiotic, pesticidal,
anticancer, and enzyme-inhibitory properties [4, 5]. Several
pharmaceutical agents are widely used in contemporary
clinical practice, including Cidofovir – а well-known
antiviral drug, Risedronic acid – a medication for treating
osteoporosis, Fosfomycin – a broad-spectrum antibiotic,
and Glyphosate – a systemic herbicide.
Results and Discussion
Organophosphorus compounds containing a P-C bond
Received:
Revised:
Accepted:
Published online:
05.10.2025
28.10.2025
04.11.2025
30.12.2025
Corresponding author. Tel.: +380-50-870-4187;
e-mail: nastya_k11@ukr.net (A.O. Kolodiazhna)
ORCID: 0000-0002-7990-7830
were first isolated from living organisms in 1959 [1, 2].
Soon afterwards many kinds of related compounds were
found in hundreds of aquatic and terrestrial animals and
microorganisms [3]. α-Hydroxyphosphonic esters, conside-
red as an important class of biologically active compounds,
have attracted attention because of their antibacterial,
antiviral, antibiotic, pesticidal, anticancer, and enzyme
inhibitor properties [4, 5].
N
N
NH2
O
O
OH
PO OH
OH
N
P
P
OH
OH
OH
OHHO
O
O
O
CH3P
O
OH
HO
H
NP
OH
OO
HO
HO
Cidofovir
Risedronic acid
FosfomycinGlyphosate
Figure 1. Examples of organophosphorus pharmaceuticals.
Phosphonic analogues of natural compounds, in which
the carboxyl group is replaced by a phosphonic
group, represent a powerful tool in modern medicinal and
© Kolodiazhna A.O. et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits
unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
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ISSN 1814-9758. Ukr. Bioorg. Acta, 2025, Vol. 20, N 2
54
bioorganic chemistry. Such a substitution imparts unique
biochemical and pharmacokinetic properties to the
molecules, including resistance to enzymatic hydrolysis and
the ability to mimic key transition states in enzymatic
reactions. Owing to these distinctive features, phosphonic
analogues of natural compounds are widely employed in
biological and medical research as enzyme inhibitors,
receptor probes, model compounds for studying amino acid
transport, biochemical probes, and stable mimetics [6-8].
Therefore, the development and optimization of methods
for obtaining phosphonic analogues of natural compounds
is an important and timely task in contemporary organic and
bioorganic chemistry.
Homoproline - a homolog of the natural amino acid
proline – and α-hydroxyhomoproline are promising chiral
building blocks and biomimetics of proline and
hydroxyproline. They possess important properties that
have enabled their application in various fields, including
use as model compounds in biological studies, as chiral
building blocks for the synthesis of enzyme inhibitors, and
in the production of pharmaceutical agents and certain
catalysts [9-12]. Therefore, we set out to obtain both
enantiomers of the phosphonic analogues of (S)- and (R)-α-
hydroxyhomoproline. These compounds have not been
synthesized previously.
N
H
OH
O
N
H
OH
O
N
H
OH
O
OH
N
H
OH
O
OH
(S)-Homoproline (R)-Homoproline
(R)-a-Hydroxy-homoproline(S)-a-Hydroxy-homoproline
Figure 2. Homoproline and α-hydroxyhomoproline.
In our work, we obtained both enantiomers of the
phosphonic analogues of α-hydroxyhomoproline. Although
similar structures had previously been synthesized by
related methods, they had not been studied or described
using physicochemical techniques such as NMR, LC-MS,
and optical rotation measurements until now [13-16]. In our
research, we used the (S)- and (R)-stereoisomers of N-Boc-
prolinol (1-(S), 1-(R)) as starting materials. Thus, (R)- and
(S)-prolinol were converted into the corresponding
aldehydes via Swern oxidation in the presence of Et₃N in
DMSO. The reaction proceeded with quantitative yield and
preserved both the optical purity and the absolute
configuration of the asymmetric carbon atom, which was
confirmed by comparison of the optical rotation values with
literature data. In this way, (R)- and (S)-N-Boc-prolinal (2-
(S), 2-(R)) were obtained.
The resulting (R)- and (S)-N-Boc-prolinal 2 were then
subjected to the Abramov reaction. The aldehydes were
mixed with diethyl phosphite in the presence of a catalytic
amount of diazabicycloundecene (DBU) as a base and
stirred at room temperature overnight. The reaction was
carried out solvent-free.
Upon completion, the reaction mixture was purified by
column chromatography on silica gel and further
crystallized from an MTBE-THF mixture. As a result, both
stereoisomers of diethyl (N-Boc-pyrrolidine)-1-hydroxy-
methylphosphonate (3-(S), 3-(R)) were obtained as a white
crystalline powder and were fully characterized using all
available physicochemical methods.
Next, the obtained diethyl hydroxyphosphonates 3 were
subjected to hydrolysis with trimethylsilyl bromide in
dichloromethane. The reaction mixture was stirred over-
night at room temperature, protected completely from light.
After completion, the mixture was evaporated and kept
under high vacuum (0.1 mmHg) to remove residual
trimethylsilyl bromide. The residue contained (S)- and (R)-
pyrrolidine-1-hydroxymethylphosphonic acids 4. These
were obtained as yellowish crystals in quantitative yields
(95%), and were characterized using all available analytical
methods. It is also important to note that such pyrrolidine-1-
hydroxymethylphosphonic acids had not been previously
obtained, neither as racemates nor in optically active forms.
Thus, both enantiomers of (S)- and (R)-diethyl-(N-Boc-
pyrrolidine)-1-hydroxymethylphosphonates were characte-
rized for the first time, and both enantiomers of (S)- and
(R)-pyrrolidine-1-hydroxymethylphosphonic acids – the
phosphonic analogues of homoproline with potential
biological activity – were synthesized and described as the
first known example.
N
O O
OH
N
O O
O
N
O O
OH
P O
O O
N
OH
P OH
HO O
**
*
PySO3, Et3N
DMCO, 80% DBU, 70%
1-(S)
1-(R)
2-(S)
2-(R)
3-(S)
3-(R)
Me3SiBr, DCM
rt, overnight, 95% *
4-(S)
4-(R)
(EtO)2P(O)H
Figure 3. Scheme of the synthesis of (S)- and (R)-pyrrolidine-1-hydroxymethylphosphonic acids.
A.O. Kolodiazhna et al.
55
Figure 4. 1H NMR and 31P NMR spectra of (S)-diethyl (N-Boc-pyrrolidine)-1-hydroxymethylphosphonate 3.
Conclusions
In this work, we obtained and described both optical
isomers, (S)- and (R)-diethyl-(N-Boc-pyrrolidine)-1-hyd-
roxymethylphosphonates, as well as (S)- and (R)-pyrroli-
dine-1-hydroxymethylphosphonic acids. To achieve this,
we employed the phosphorylation of the corresponding
carbonyl compounds via the Abramov reaction. All
ISSN 1814-9758. Ukr. Bioorg. Acta, 2025, Vol. 20, N 2
56
synthesized diethyl-(N-Boc-pyrrolidine)-1-hydroxymethyl-
phosphonates were characterized for the first time using all
available physicochemical methods. Subsequently, the
obtained diethyl-(N-Boc-pyrrolidine)-1-hydroxymethyl-
phosphonates were converted into optically pure (S)- and
(R)-pyrrolidine-1-hydroxymethylphosphonic acids with
complete retention of absolute configuration. Both optically
active (S)- and (R)-pyrrolidine-1-hydroxymethylphosphonic
acids were produced for the first time in high chemical
yields, with optical purity <95%, and were fully described
and characterized using modern physicochemical
techniques. Thus, both enantiomers of diethyl-(N-Boc-
pyrrolidine)-1-hydroxymethylphosphonates and pyrroli-
dine-1-hydroxymethylphosphonic acids were obtained,
representing promising building blocks for the synthesis of
potential pharmaceuticals and biologically active
compounds.
N
O O
OH
P O
O O
N
O O
OH
P O
O O
N
H OH
P OH
HO O
N
H OH
P OH
HO O
3-(S) 3-(R)
4-(S) 4-(R)
Figure 5. Newly obtained optically active α-hydroxy-
diethylphosphonates and α-hydroxyphosphonic acids.
Experimental section
All solvents were purified according to standard
procedures. All starting materials were obtained from
Enamine LTD or other commercial suppliers. Melting
points were measured using an MPA 100 OptiMelt
automated melting point system. ¹H and ¹³C NMR spectra
were recorded in CDCl₃ on a Bruker “Avance III” 500 MHz
spectrometer (Germany) at ambient temperature. Chemical
shifts (δ) are given in parts per million relative to
tetramethylsilane (TMS) as an internal standard. Signal
multiplicities are reported as s (singlet), d (doublet), dd
(doublet of doublets), t (triplet), m (multiplet), br (broad), q
(quartet). Spin-spin coupling constants (J) are given in
hertz. Column chromatography was performed on silica gel
60 (70-230 mesh). Optical rotation was measured on a
Perkin-Elmer 241 polarimeter (sodium D line, 20 °C).
Melting points were uncorrected. All reactions were carried
out in glassware dried by flame or in a drying oven.
Reaction progress was monitored by analytical thin-layer
chromatography (TLC) on silica gel 60 F254 plates (Merck,
Germany), and products were visualized using anisaldehyde
or UV light. The purity of all compounds was evaluated by
TLC and NMR measurements.
Synthesis
General procedure for the synthesis of tert-butyl (2S)-2-for-
mylpyrrolidine-1-carboxylate.
A solution of N-Boc-prolinol (10 g, 0.05 mol, 1 eq.) in
dry DMSO (150 mL) was treated with Et₃N (20 mL, 0.15
mol, 3 eq.). The mixture was cooled to 0 °C (ice bath) with
stirring, and a suspension of Py • SO₃ (23.8 g, 0.15 mol, 3
eq.) in DMSO (50 mL) was added portionwise. The
reaction mixture was stirred at room temperature overnight.
After completion, the reaction mixture was poured into cold
water and extracted with MTBE three times. The combined
organic layers were washed with water five times to remove
residual DMSO. The organic phase was dried over sodium
sulfate and concentrated. The residue contained tert-butyl 2-
formylpyrrolidine-1-carboxylate, which was used in
subsequent transformations without further purification.
tert-Butyl (2S)-2-formylpyrrolidine-1-carboxylate (2-(S)).
Yellow oil; Yield 8.8 g, 88.8%. [a]D
20 = -100.76 (C =
1.0, CH2Cl2). 1H NMR (СDCl3, 500 MHz, 25 ºC) δ 9.53-
9.43 (m, 1H), 4.17-4.02 (m, 1H), 3.58-3.40 (m, 2H), 2.09-
1.85 (m, 4H), 1.45-1.40 (m, 9H). GCMS: m/z calcd 170.2
[M+ -CHO] for C10H17NO3 -CHO (170.1).
NMR spectrum showed a mixture of conformers
tert-Butyl (2R)-2-formylpyrrolidine-1-carboxylate (2-(R)).
Yellow oil; Yield 8.9 g, 89%. [a]D
20 = +101 (C = 1.0,
CH2Cl2). 1H NMR (СDCl3, 500 MHz, 25 ºC) δ 9,53-9,43
(m, 1H), 4.17-4.02 (m, 1H), 3.58-3.40 (m, 2H), 2.09-1.85
(m, 4H), 1.45-1.40 (m, 9H). GCMS: m/z calcd 170.2 [M+ -
CHO] for C10H17NO3 -CHO (170.1).
NMR spectrum showed a mixture of conformers
General procedure for the synthesis of diethyl 1-(N-Boc-2-
pyrrolidine)-1-hydroxymethylphosphonate.
tert-Butyl-2-formylpyrrolidine-1-carboxylate (8.8 g, 0.044
mol, 1 eq.) was mixed with (EtO)₂P(O)H (6 mL, 0.046 mol,
1.05 eq.) without solvent. DBU (0.2 mL, cat.) was added
with stirring. The reaction mixture was stirred at room
temperature overnight. The resulting product was purified
by column chromatography. As a result, diethyl 1-(N-Boc-
2-pyrrolidine)-1-hydroxymethylphosphonate was obtained
as a white crystalline solid.
(S)-diethyl 1-(N-Boc-2-pyrrolidine)-1-hydroxymethylphos-
phonate (3-(S)).
White solid; Yield 8 g, 54.5%. [a]D
20 = +57.45 (C = 0.5,
MeOH). Rf = 0.3 (eluent - EtOAc, Alugram Xtra-Sheets
SIL G/UV254, stain - anisaldehyde). 1H NMR (СDCl3, 500
MHz, 25 ºC) δ 5.47 (br s 1H), 4.17-4.11 (m, 4H), 3.54-3.48
(m, 1H), 3.35-3.28 (m, 1H), 2.29-2.19 (m, 1H), 2.09-2.02
(m, 2H), 1.73-1.64 (m, 1H), 1.45 (s, 9H), 1.33-1.29 (m,
6H). 31P NMR (СDCl3, 160 МГц, 25 ºC) δ 22.41. 13С NMR
A.O. Kolodiazhna et al.
57
Figure 6. 1H NMR and 31P NMR spectra of (S)-pyrrolidine-1-hydroxymethylphosphonic acid 4.
(125.7 МГц, СDCl3, 25 ºC) δ 154.76, 78.32, 69.47, 68.23,
60.67, 58.56, 56.55, 46.08, 45.19, 26.79, 25.93, 24.72,
22.72, 14.81. LCMS: M 238 (M+H+ -t-BuOCO) (M 337.35)
(R).
ISSN 1814-9758. Ukr. Bioorg. Acta, 2025, Vol. 20, N 2
58
(R)-diethyl 1-(N-Boc-2-pyrrolidine)-1-hydroxymethylphos-
phonate (3-(R)).
White solid; Yield 8.2 g, 55.3%. [a]D
20 = -57.34 (C = 0.5,
MeOH).Rf = 0.3 (eluent - EtOAc, Alugram Xtra-Sheets SIL
G/UV254, stain - anisaldehyde). 1H NMR (СDCl3, 500
MHz, 25 ºC) δ 5.47 (br s 1H), 4.17-4.11 (m, 4H), 3.54-3.48
(m, 1H), 3.35-3.28 (m, 1H), 2.29-2.19 (m, 1H), 2.09-2.02
(m, 2H), 1.73-1.64 (m, 1H), 1.45 (s, 9H), 1.33-1.29 (m,
6H). 31P NMR (СDCl3, 160 МГц, 25 ºC) δ 22.41. 13С NMR
(125.7 МГц, СDCl3, 25 ºC) δ 154.76, 78.32, 69.47, 68.23,
60.67, 58.56, 56.55, 46.08, 45.19, 26.79, 25.93, 24.72,
22.72, 14.81. LCMS: M 238 (M+H+-t-BuOCO) (M
337.35)(R).
General procedure for the synthesis of (2-pyrrolidine)-1-
hydroxymethylphosphonic acid hydrochloride.
Diethyl 1-(N-Boc-2-pyrrolidine)-1-hydroxymethylphos-
phonate was dissolved in dry dichloromethane, and
Me₃SiBr was added under cooling. The reaction mixture
was stirred at room temperature in complete darkness. Upon
completion, the solvent was evaporated, and the residue was
dissolved in THF, followed by the addition of dioxane·HCl
(10 N, 2 eq.). The solvent was evaporated again, and the
remaining crystalline material was purified by washing the
solid with THF. As a result, (2-pyrrolidine)-1-hydroxy-
methylphosphonic acid HCl was obtained as a yellowish
powder.
(S)-(2-pyrrolidine)-1-hydroxymethylphosphonic acid hydro-
chloride (4-(S)).
Yellowish powder; Yield 3.5 g, 67%. [a]D
20 = -20.27 (C
= 0.5, MeOH). 1H NMR (DMSO-d6, 500 MHz, 25 ºC) δ
9.24 (br s, 1H), 8.34 (br s, 1H), 4.05-3.98 (m, 1H), 3.74-
3.64 (m, 1H), 3.15-3.05 (m, 2H), 2.01-1.74 (m, 4H). 31P
NMR (DMSO-d6, 160 МГц, 25 ºC) δ 17.27. 13С NMR
(125.7 МГц, DMSO-d6, 25 ºC) δ 66.53, 64.92, 45.37, 24.74,
23.99.
(R)-(2-pyrrolidine)-1-hydroxymethylphosphonic acid hydro-
chloride (4-(R)).
Yellowish powder; Yield 3.8 g, 72.8%. [a]D
20 = +21.32
(C = 0.5, MeOH). 1H NMR (DMSO-d6, 500 MHz, 25 ºC) δ
9.24 (br s, 1H), 8.34 (br s, 1H), 4.04-3.98 (m, 1H), 3.74-
3.64 (m, 1H), 3.15-3.05 (m, 2H), 2.01-1.74 (m, 4H). 31P
NMR (DMSO-d6, 160 МГц, 25 ºC) δ 17.28. 13С NMR
(125.7 МГц, DMSO-d6, 25 ºC) δ 66.53, 64.92, 45.37, 24.74,
23.99.
Notes
Acknowledgments. We would like to thank Enamine
Ltd. for the material and technical support for the synthetic
part of this work. The authors thank all the brave defenders
of Ukraine who stood against the russian full-scale invasion
and made this publication possible.
The authors declare no conflict of interest.
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59
Синтез нових α-гідроксифосфонових кислот – фосфорних аналогів гомопроліну
А.О. Колодяжна*, Д.В. Присяжнюк, Є.В. Гришкун.
Інститут біоорганічної хімії та нафтохімії ім. В.П. Кухаря НАН України, Київ, Україна
Резюме: Розроблено синтетичний підхід до синтезу нових біоізостерів гомопроліну – α-гідроксифосфонових кислот. На ключових етапах
використано реакцію фосфорилювання карбонільних похідних (S)- та (R)-проліну – реакцію Абрамова. Отримані α-гідроксифосфонові кислоти
можуть бути потенційно біологічно активними речовинами для розробки нових фармацевтичних препаратів.
Ключові слова: α-гідроксифосфонова кислота; фосфорні аналоги амінокислот; реакція Абрамова; біологічна активність.
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| id | oai:ojs2.bioorganica.com.ua:article-125 |
| institution | Ukrainica Bioorganica Acta |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-06-30T01:00:25Z |
| publishDate | 2025 |
| publisher | V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine |
| record_format | ojs |
| resource_txt_mv | bioorganicacomua/e0/04f713f14f12bb283cd8bb270ab6e2e0.pdf |
| spelling | oai:ojs2.bioorganica.com.ua:article-1252026-06-29T16:07:07Z Synthesis of new α-hydroxyphosphonic acids – phosphorus analogues of homoproline Синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну Kolodiazhna, Anastasiia O. Prysiazhnuk, Dmytro V. Gryshkun, Yevgen V. α-hydroxyphosphonic acid phosphorus analogs of amino acids Abramov reaction biological activity α-гідроксифосфонова кислота фосфорні аналоги амінокислот реакція Абрамова біологічна активність A synthetic approach has been developed for the preparation of new bioisosteres of homoproline, namely α-hydroxyphosphonic acids. At the key stages of the synthesis, the phosphorylation of carbonyl derivatives of (S)- and (R)-proline via the Abramov reaction was employed. The resulting α-hydroxyphosphonic acids are promising compounds with, potential biologicalactivity and may serve as valuable candidates for the development of new pharmaceuticals and physiologically active compounds&nbsp; Розроблено синтетичний підхід до синтезу нових біоізостерів гомопроліну - α-гідроксифосфонових кислот. На ключових етапах використано реакцію фосфорилювання карбонільних похідних (S)- та (R)-проліну - реакцію Абрамова. Отримані α-гідроксифосфонові кислоти можуть бути перспективними потенційно біологічно активними речовинами для розробки нових фармацевтичних препаратів та фізіологічно активних сполук V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2025-12-31 Article Article application/pdf https://bioorganica.com.ua/index.php/journal/article/view/125 10.15407/bioorganica2025.02.053 Ukrainica Bioorganica Acta; Vol. 20 No. 2 (2025): Ukrainica Bioorganica Acta; 53-59 Ukrainica Bioorganica Acta; Том 20 № 2 (2025): Ukrainica Bioorganica Acta; 53-59 1814-9766 1814-9758 10.15407/bioorganica2025.02 en https://bioorganica.com.ua/index.php/journal/article/view/125/108 Copyright (c) 2025 Anastasiia O. Kolodiazhna, Dmytro V. Prysiazhnuk, Yevgen V. Gryshkun https://creativecommons.org/licenses/by/4.0 |
| spellingShingle | α-гідроксифосфонова кислота фосфорні аналоги амінокислот реакція Абрамова біологічна активність Kolodiazhna, Anastasiia O. Prysiazhnuk, Dmytro V. Gryshkun, Yevgen V. Синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну |
| title | Синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну |
| title_alt | Synthesis of new α-hydroxyphosphonic acids – phosphorus analogues of homoproline |
| title_full | Синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну |
| title_fullStr | Синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну |
| title_full_unstemmed | Синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну |
| title_short | Синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну |
| title_sort | синтез нових α-гідроксифосфонових кислот - фосфорних аналогів гомопроліну |
| topic | α-гідроксифосфонова кислота фосфорні аналоги амінокислот реакція Абрамова біологічна активність |
| topic_facet | α-hydroxyphosphonic acid phosphorus analogs of amino acids Abramov reaction biological activity α-гідроксифосфонова кислота фосфорні аналоги амінокислот реакція Абрамова біологічна активність |
| url | https://bioorganica.com.ua/index.php/journal/article/view/125 |
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