Synthesis and Mass Spectrometry of 2-Hydroxyethyl 1-Aminoalkylphosphonates

Cai, Shuzong; Yin, Wei; Ma, Yuan; Liu, Han; Zhao, Yufen; Xu, Jiaxi

doi:10.1080/10426500600865251

Cited by 13 publications

(5 citation statements)

References 16 publications

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“…Multiple component condensation reactions are efficient methods for construction of structurally diverse products. Our developed pseudo four component condensation reactions of amides, aldehydes, and phosphorus reagents followed by hydrolysis, aminolysis, and alcoholysis have been applied in the synthesis of various α‐aminoalkylphosphonic acid derivatives [35–38] . and phosphonopeptides [39,40] .…”

Section: Synthesis Of α‐Phosphinopeptides and α‐Phosphinodepsipeptidesmentioning

confidence: 99%

“…Our developed pseudo four component condensation reactions of amides, aldehydes, and phosphorus reagents followed by hydrolysis, aminolysis, and alcoholysis have been applied in the synthesis of various α-aminoalkylphosphonic acid derivatives. [35][36][37][38] and phosphonopeptides. [39,40] A series of phosphinopeptides were synthesized via the Mannich-type reaction of aryldichlorophosphines, aldehydes, and N-protected amino amides and subsequent aminolysis with amino esters.…”

Section: Synthesis Of α-Phosphinopeptides Via the Four Component Cond...mentioning

confidence: 99%

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Synthesis of Phosphinopeptides and Phosphinodepsipeptides

2020

Asian J Org Chem

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Both phosphinopeptides and phosphinodepsipeptides are important phosphorus analogues of naturally occurring peptides. They have been widely applied as biological active peptides, such as enzyme inhibitors, haptens for production of catalytic antibodies, and antibiotics. Synthetic methods of phosphinopeptides and phosphinodepsipeptides are reviewed and classified on the basis of the structural characteristics of aminoalkylphosphinic acids. This review focuses on the synthetic methods to phosphinopeptides and phosphinodepsipeptides, including α‐, β‐, and γ‐phosphinopeptides and α‐phosphinodepsipeptides.

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Section: Synthesis Of α‐Phosphinopeptides and α‐Phosphinodepsipeptidesmentioning

confidence: 99%

Section: Synthesis Of α-Phosphinopeptides Via the Four Component Cond...mentioning

confidence: 99%

Synthesis of Phosphinopeptides and Phosphinodepsipeptides

2020

Asian J Org Chem

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“…NMR spectral characteristics of aminophosphonic acids and their derivatives are an important and common tool both for determination of structure peculiarities of aminophosphonic acids and identification of new and known compounds in reaction mixtures and biological samples [10]. For example, 31 P-NMR analysis has been successfully used to detect and discriminate aminophosphonic acids AEP 1 and MeNHCH 2 CH 2 P(O)(OH) 2 from other phosphoric acid derivatives in sea animals [11]. The solid-state 31 P-NMR cross-polarization magic angle spinning technique enables determination of the amount of CÀP forms in the total phosphorus in sea anemones [12].…”

Section: Physical/chemical Properties and Analysismentioning

confidence: 99%

“…In recent years several improved procedures for the preparation of N-protected a-aminoalkylphosphonates have been reported [28][29][30][31][32][33]. For example, diphenyl a-aminomethylphosphonates R 3 OC(O)NHCR 1 R 2 P(O)(OPh) 2 have been synthesized in good yields by a Lewis acid-catalyzed reaction of a carbamate, a carbonyl compound, and triphenyl phosphite [34].…”

Section: Amidoalkylation In the Carbonyl Compound-amine-phosphite Thrmentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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“…1-(N-Cbz-amino)arylmethylphosphonate ethylene glycol cyclic diesters and linear monoesters show different fragmentation under ESI conditions. 16 We investigated the mass spectrometric behavior of 1-(N-Cbz-amino)arylmethylphosphonate phenyl monoesters (Scheme 1) and found they showed remarkably different fragmentation patterns from the corresponding methyl and ethyl monoesters under positive ESI conditions. In this article, we present the ESI-MS n fragmentation of 1-(N-Cbz-amino)arylmethylphosphonate phenyl monoesters.…”

Section: Introductionmentioning

confidence: 99%

Abundant Intramolecular Ring Rearrangements of 1-(N-Benzyloxycarbonylamino)arylmethylphosphonate Phenyl monoesters Under Electrospray Ionization Conditions

2011

Phosphorus, Sulfur, and Silicon and the Related Elements

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The mass spectrometric behavior of 1-(N-benzyloxycarbonylamino)arylmethylphosphonate phenyl monoesters was investigated under positive ion electrospray ionization conditions. All nitrogen-protonated title compounds undergo four-and/or six-membered ring rearrangements to yield nitrogen-containing fragment ions by consecutive or simultaneous loss of a carbon dioxide and phenyl hydrogen phosphonate or phenyl benzylphosphonate or an arylmethylimine. All oxygen-protonated title compounds undergo four-to six-membered ring rearrangements to produce fragment ions by loss of a carbon dioxide plus an arylmethylimine, or phenyl benzylphosphonate, by consecutive or simultaneous loss of benzyl phenyl ether and isocyanic acid. The fragmentation is obviously different from the corresponding methyl and ethyl monoesters, which show a tendency to undergo intramolecular four-membered ring rearrangements only.

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Synthesis and Mass Spectrometry of 2-Hydroxyethyl 1-Aminoalkylphosphonates

Abstract: phonate monoesters were obtained exclusively after the addition of water under stirring. The reaction mechanism was discussed. Their mass spectrometric fragmentations were also described.

Cited by 13 publications

References 16 publications

Synthesis of Phosphinopeptides and Phosphinodepsipeptides

Synthesis of Phosphinopeptides and Phosphinodepsipeptides

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Abundant Intramolecular Ring Rearrangements of 1-(N-Benzyloxycarbonylamino)arylmethylphosphonate Phenyl monoesters Under Electrospray Ionization Conditions

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