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Article

Synthesis of Four Enantiomers of (1-Amino-3-Hydroxypropane-1,3-Diyl)Diphosphonic Acid as Diphosphonate Analogues of 4-Hydroxyglutamic Acid

by
Liwia Lebelt
,
Iwona E. Głowacka
and
Dorota G. Piotrowska
*
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(9), 2699; https://doi.org/10.3390/molecules27092699
Submission received: 5 April 2022 / Revised: 20 April 2022 / Accepted: 21 April 2022 / Published: 22 April 2022
(This article belongs to the Special Issue Design, Synthesis, and Analysis of Potential Drugs, 2nd Edition)
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Abstract

All the enantiomers of (1-amino-3-hydroxypropane-1,3-diyl)diphosphonic acid, newly design phosphonate analogues of 4-hydroxyglutamic acids, were obtained. The synthetic strategy involved Abramov reactions of diethyl (R)- and (S)-1-(N-Boc-amino)-3-oxopropylphosphonates with diethyl phosphite, separation of diastereoisomeric [1-(N-Boc-amino)-3-hydroxypropane-1,3-diyl]diphosphonates as O-protected esters, followed by their hydrolysis to the enantiomeric phosphonic acids. The absolute configuration of the enantiomeric phosphonates was established by comparing the 31P NMR chemical shifts of respective (S)-O-methylmandelic acid esters obtained from respective pairs of syn- and anti-[1-(N-Boc-amino)-3-hydroxypropane-1,3-diyl]diphosphonates according to the Spilling rule.
Keywords: Abramov reaction; phosphonates; glutamic acid analogues; absolute configuration Abramov reaction; phosphonates; glutamic acid analogues; absolute configuration
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MDPI and ACS Style

Lebelt, L.; Głowacka, I.E.; Piotrowska, D.G. Synthesis of Four Enantiomers of (1-Amino-3-Hydroxypropane-1,3-Diyl)Diphosphonic Acid as Diphosphonate Analogues of 4-Hydroxyglutamic Acid. Molecules 2022, 27, 2699. https://doi.org/10.3390/molecules27092699

AMA Style

Lebelt L, Głowacka IE, Piotrowska DG. Synthesis of Four Enantiomers of (1-Amino-3-Hydroxypropane-1,3-Diyl)Diphosphonic Acid as Diphosphonate Analogues of 4-Hydroxyglutamic Acid. Molecules. 2022; 27(9):2699. https://doi.org/10.3390/molecules27092699

Chicago/Turabian Style

Lebelt, Liwia, Iwona E. Głowacka, and Dorota G. Piotrowska. 2022. "Synthesis of Four Enantiomers of (1-Amino-3-Hydroxypropane-1,3-Diyl)Diphosphonic Acid as Diphosphonate Analogues of 4-Hydroxyglutamic Acid" Molecules 27, no. 9: 2699. https://doi.org/10.3390/molecules27092699

APA Style

Lebelt, L., Głowacka, I. E., & Piotrowska, D. G. (2022). Synthesis of Four Enantiomers of (1-Amino-3-Hydroxypropane-1,3-Diyl)Diphosphonic Acid as Diphosphonate Analogues of 4-Hydroxyglutamic Acid. Molecules, 27(9), 2699. https://doi.org/10.3390/molecules27092699

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