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Asymmetric synthesis of \(\boldsymbol{\gamma}\)-aminophosphonates: The bio-isosteric analogs of \(\boldsymbol{\gamma}\)-aminobutyric acid

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Abstract

The properties of aminophosphonates as transition state analogs of amino acids, and as antibacterial, antifungal and antiHIV agents attracted considerable attention in recent years. Although many reviews appeared in the literature covering α- and β-aminophosphonates, γ-aminophosphonates did not receive sufficient attention despite the fact that parent γ-aminophosphonic acid and its derivatives are bio-isosteric analogs of GABA (γ-amino butyric acid). This review provides a critical summary of the significance of γ-aminophosphonates and various approaches to their synthesis, with particular emphasis to asymmetric versions.

The properties of aminophosphonates as transition state analogs of amino acids, and as anti-bacterial, antifungal and antiHIV agents attracted considerable attention. γ-Aminophosphonic acid in particular is a bio-isosteric analog of GABA (γ-aminobutyric acid).

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Acknowledgements

INNN thanks the Department of Science and Technology (DST), India, and Board of Studies in Nuclear Sciences (BRNS), India, for financially supporting research in the area of amino/nitrophosphonates. KB thanks the Council of Scientific and Industrial Research (CSIR) for a Senior Research Fellowship and DN thanks DST for a Postdoctoral Fellowship. The authors thank Prof. Mahesh K Lakshman, The City University of New York, for his encouragement and support.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India

    KALISANKAR BERA, DWAYAJA NADKARNI & IRISHI N N NAMBOOTHIRI

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  1. KALISANKAR BERA
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Abbreviations

Abbreviations

APCPr:

1-Amino-2-phosphonomethylcyclo- propanecarboxylic acid

N-AcDMPT:

N-Acetyldemethyl phosphinothricin

N-AcDMPTT:

N-Acetyldemethyl phosphinothricin tripeptide

S-BINAM:

(S)-(-)-1,1′-Binaphthalene-2,2′-diamine

CDI:

1,1′-Carbonyldiimidazole

DDQ:

2,3-Dichloro-5,6-dicyano-1, 4-benzoquinone

DIAD:

Diisopropyl azodicarboxylate

DMAP:

4-Dimethylaminopyridine

DMP:

Dess–Martin periodinane

DMPU:

N,N′-Dimethyl-N,N′-trimethyl-eneurea

DPPA:

Diphenylphosphoryl azide

GABA:

γ-Aminobutyric acid

GAPA:

γ-Aminophosphonic acid

HMPA:

Hexamethylphosphoramide

LDA:

Lithium di-isopropylamide

LiHMDS:

Lithium hexamethyldisilazide

MPLC:

Medium pressure liquid chromatography

NMM:

N-Methylmorpholine

NaHMDS:

Sodium hexamethyldisilazide

PCC:

Pyridinium chlorochromate

PTSA:

p-Toluene sulphonic acid

TBAF:

Tetra-n-butylammonium fluoride

TBDMS:

Tert-butyldimethylsilyl

THF:

Tetrahydrofuran

TMEDA:

Tetramethylethylenediamine

TMSBr:

Trimethylsilyl bromide

TMSI:

Trimethylsilyl iodide

TMSN3 :

Trimethylsilyl azide

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BERA, K., NADKARNI, D. & NAMBOOTHIRI, I.N.N. Asymmetric synthesis of \(\boldsymbol{\gamma}\)-aminophosphonates: The bio-isosteric analogs of \(\boldsymbol{\gamma}\)-aminobutyric acid. J Chem Sci 125, 443–465 (2013). https://doi.org/10.1007/s12039-013-0418-6

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