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Search for "amino acid derivatives" in Full Text gives 89 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

  • Friederike I. Nollmann,
  • Andrea Dowling,
  • Marcel Kaiser,
  • Klaus Deckmann,
  • Sabine Grösch,
  • Richard ffrench-Constant and
  • Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

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  • sequence was synthesized on a preloaded 2-chlorotrityl chloride resin (Carbolution Chemicals, Germany) on a 50 μmol scale with the Discover CEM System by using standard 9-fluorenylmethoxycarbonyl/tert-butyl (Fmoc/t-Bu) chemistry. An amount of 6 equiv of amino-acid derivatives (>98%; Iris Biotech, Germany
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Letter
Published 11 Apr 2012

Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines

  • Melinda Nonn,
  • Loránd Kiss,
  • Reijo Sillanpää and
  • Ferenc Fülöp

Beilstein J. Org. Chem. 2012, 8, 100–106, doi:10.3762/bjoc.8.10

Graphical Abstract
  • cispentacin stereoisomer 2 into multifunctionalized β-amino acid derivative 12. Synthesis of multifunctionalized β-amino acid derivatives 13–16. Reaction conditions: NaBH4, NiCl2, Boc2O, EtOH/H2O, rt, 6 h. Acknowledgements We are grateful to the Hungarian Research Foundation (OTKA No. T81371) for financial
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Published 17 Jan 2012

Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

  • Elizabeth P. Jones,
  • Peter Jones,
  • Andrew J. P. White and
  • Anthony G. M. Barrett

Beilstein J. Org. Chem. 2011, 7, 1570–1576, doi:10.3762/bjoc.7.185

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Published 25 Nov 2011

Ratiometric fluorescent probe for enantioselective detection of D-cysteine in aqueous solution

  • Xiao-bo Zhou,
  • Wing-Hong Chan,
  • Albert W. M. Lee and
  • Chi-Chung Yeung

Beilstein J. Org. Chem. 2011, 7, 1508–1515, doi:10.3762/bjoc.7.176

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  • enantioselectivity on Cys for the first time. Experimental Proton NMR spectra were recorded on a Bruker Avance-III 400 spectrometer at 400 MHz in DMSO-d6. Fluorescence emission spectra and UV–vis spectra were collected on a PE LS50B and a Cary UV-100 spectrometer, respectively. All inorganic reagents and amino acid
  • derivatives were of analytical reagent grade and were obtained from Aldrich or Sigma. ACAQ was synthesized according to our method [16]. The stock solution of 1.0 × 10−3 M ACAQ was obtained by dissolution of the compound in ACN. The stock solutions of 5.0 × 10−3 M amino acids were prepared by dissolution of
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Published 09 Nov 2011

A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions

  • Ameer F. Zahoor,
  • Sarah Thies and
  • Uli Kazmaier

Beilstein J. Org. Chem. 2011, 7, 1299–1303, doi:10.3762/bjoc.7.151

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  • conclusion, we showed that the ring opening of epoxides, either directly or Pd-catalyzed, with chelated enolates combined with Passerini reactions is a suitable tool for the synthesis of highly functionalized α-hydroxy and α-amino acid derivatives. These new compounds are interesting building blocks for
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Published 19 Sep 2011

Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles

  • Peter Wipf and
  • Marija D. Manojlovic

Beilstein J. Org. Chem. 2011, 7, 824–830, doi:10.3762/bjoc.7.94

Graphical Abstract
  • of the Boc-protected aminopyran ring in 21. One-pot hydrozirconation-reductive coupling of allene 2 and nitrile 7. Cyclization of allenylnitrile 18. Proposed chelated transition state model. Conversion of homoallylic amines to β-amino acid derivatives. Reaction of N-aluminoimines with
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Published 17 Jun 2011

Anthracene appended pyridinium amide–urea conjugate in selective fluorometric sensing of L-N-acetylvaline salt

  • Kumaresh Ghosh,
  • Tanmay Sarkar and
  • Asoke P. Chattopadhyay

Beilstein J. Org. Chem. 2010, 6, 1211–1218, doi:10.3762/bjoc.6.139

Graphical Abstract
  • to the charge–charge interaction and formation of unconventional hydrogen bonds with the anionic guests [27]. In order to explore this binding site for a wide range of substrates, especially for amino acid derivatives, we report here the design and synthesis of a new fluororeceptor 1 where anthracene
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Published 21 Dec 2010

En route to photoaffinity labeling of the bacterial lectin FimH

  • Thisbe K. Lindhorst,
  • Michaela Märten,
  • Andreas Fuchs and
  • Stefan D. Knight

Beilstein J. Org. Chem. 2010, 6, 810–822, doi:10.3762/bjoc.6.91

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  • scaffold molecule in two different ways in order to allow fine-tuning of the spacing between the mannoside ligand and the photoactive group. Thus, the amino acid derivatives Fmoc-Asp-OtBu and Fmoc-Asp(OtBu)-OH were employed in two analogous synthetic pathways, starting with peptide coupling to the known 2
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Published 26 Aug 2010

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

  • Norio Shibata,
  • Andrej Matsnev and
  • Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

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  • the synthesis of sugar and amino acid derivatives. Reagents 35 and 37 have been identified as mild and efficient trifluoromethylating reagents for primary and secondary aryl- and alkylphosphines. Both reacted with equal efficiency at −78 °C to rt without any added base since the reagents generate base
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Published 16 Jun 2010

Molecular recognition of organic ammonium ions in solution using synthetic receptors

  • Andreas Späth and
  • Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

Graphical Abstract
  • crown macrocycles have been developed by Lee et al. [154] who studied their enantiomeric recognition properties towards a number of amino acid derivatives and chiral organic ammonium salts using UV–vis and NMR methods. The macrocycles were found to be strong chelating agents for primary organic ammonium
  • values with triamine 45c. Based on this phenolphthalein skeleton, the host was later further developed for use in visual enantiomeric discrimination [185] (Figure 28). Various types of chiral host molecules were examined for their enantioselective color effect in complexation with chiral amino acid
  • derivatives in methanol solution. The methyl substituted compound (S,S,S,S)-46a showed a particularly prominent selectivity for the alanine amide derivatives with 1,5-pentane diamine and 1,6-hexane diamine: A combination of methyl substituted host (S,S,S,S)-46a with the R-enantiomers developed a purple color
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Published 06 Apr 2010

Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones

  • Heloise Brice,
  • Jonathan Clayden and
  • Stuart D. Hamilton

Beilstein J. Org. Chem. 2010, 6, No. 22, doi:10.3762/bjoc.6.22

Graphical Abstract
  • scope of the dearomatisation can be extended to much less reactive nucleophiles with a more electron deficient aromatic acceptor [39][40][41]. Thus enolates of glycine esters 1 carrying isonicotinoyl or nicotinoyl N-substituents cyclise readily to yield bicyclic amino acid derivatives 2 (Scheme 1a for
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Published 02 Mar 2010

Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton

  • Matthias Breuning,
  • Tobias Häuser,
  • Christian Mehler,
  • Christian Däschlein,
  • Carsten Strohmann,
  • Andreas Oechsner and
  • Holger Braunschweig

Beilstein J. Org. Chem. 2009, 5, No. 81, doi:10.3762/bjoc.5.81

Graphical Abstract
  • -C2 side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.02,6]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for
  • ][8] are embedded in peptidomimetics (Figure 1). Enantioselective organocatalysis [9][10][11][12][13][14][15][16][17] is another field of application for conformationally rigid amino acid derivatives. In this context, focus was also put on derivatives in which the activating acidic group is anchored
  • reactions. Our studies targeted the chiral, tricyclic amino acid derivatives 7 and 8 (Figure 2), which possess a central norbornane framework equipped with a 2-endo,3-endo-annelated pyrrolidine ring. Due to the constrained, bowl-shaped backbone, these compounds may possess high potential as β-turn-inducing
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Published 21 Dec 2009

The use of chiral lithium amides in the desymmetrisation of N-trialkylsilyl dimethyl sulfoximines

  • Matthew J. McGrath and
  • Carsten Bolm

Beilstein J. Org. Chem. 2007, 3, No. 33, doi:10.1186/1860-5397-3-33

Graphical Abstract
  • aryl-alkylsulfoximines are generally prepared by resolution with camphorsulfonic acid but this method is not applicable to dialkyl sulfoximines. [5][6][7] Imination of enantioenriched sulfoxides and derivatisation of sulfoximines with enantiomerically pure amino acid derivatives also provide
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Published 16 Oct 2007

Reactions of glycidyl derivatives with ambident nucleophiles; part 2: amino acid derivatives

  • Gerald Dyker,
  • Andreas Thöne and
  • Gerald Henkel

Beilstein J. Org. Chem. 2007, 3, No. 28, doi:10.1186/1860-5397-3-28

Graphical Abstract
  • achieved the annulation reaction of amino acid derivatives with glycidyl compounds as functionalized C3 building blocks in combination with a cobalt-catalyzed addition of anilines to the epoxide functionality. This rather selective transition-metal catalysed step builds up the alcohol and the amino
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Published 27 Sep 2007
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