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Beyond Azathiocoraline: Synthesis of Analogues

  • Núria Bayó-Puxan
  • Ariadna Fernández
  • Judit Tulla-Puche
  • Estela Riego
  • Mercedes Álvarez
  • Fernando Albericio
Bruce Merrifield Commemorative Issue

Summary

Azathiocoraline synthesis has been developed and optimized by using the solid-phase approach. This convenient solid-phase methodology, which involves more steps on solid-phase, has been successfully applied for generating Azathiocoraline analogues. The solid-phase approach consolidates a rapid and efficient way to explore synthetic strategies for new bioactive, highly non-proteinogenic complex depsipeptides and is an essential tool to shorten the development time required for new therapeutic compounds.

Antitumoral compound  coupling reagent  marine origin compounds  peptide protecting group 

Abbreviations

Acm

acetamidomethyl group

Barlos resin or CTC resin

2-chlorotrityl chloride resin

Boc

tert-butoxycarbonyl

DBU

1,8-diazabicyclo[5.4.0]undec-7-ene

DCM

dichloromethane

DHB

dihydroxybenzoic acid

DIEA

N,N-diisopropylethylamine

DIPCDI

N,N′-diisopropylcarbodiimide

DMF

N,N-dimethylformamide

EDC·HCl

3-(3-dimethylaminopropyl)-1-ethylcarbodiimide

Fmoc

fluorenylmethoxycarbonyl

ES(+)MS

positive electrospray mass spectroscopy

HATU

1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5-b]pyridinium hexafluorophosphate 3-oxide

HFA

hexafluoroacetone

HOAt

1-hydroxy-7-azabenzotriazole

HOBt

1-hydroxybenzotriazole

HOSu

N-hydroxysuccinimide

HPLC

high performance liquid chromatography

3HQA

3-hydroxyquinaldic acid

MALDI-TOF

matrix-assisted laser desorption

MTBD

1,3,4,6,7,8-Hexahydro-1-methyl-2H-pyrimido[1,2-a]pyrimide

NMR

nuclear magnetic resonance

o-NBS

o-nitrobenzenesulfonyl group

PyAOP

(7-azabenzotraizol-1-yloxy)-tris(pyrrolidino)phosphonium hexafluorophosphate

QNA

quinaldic acid

2QXA

2-quinoxalinecarboxylic acid

SPM

solid-phase N-methylation

TBME

tert-butyldimethylether

TES

triethylsilane

TFA

trifluoroacetic acid

THF

tetrahydrofuran

tR

retention time. Amino acid symbols denote the l-configuration unless stated otherwise. All solvent ratios are volume/volume unless stated otherwise.

Notes

Acknowledgments

This study was partially supported by CICYT (CTQ2006-03794/BQU), the Generalitat of Catalonia (2005SGR 00662), and the Barcelona Science Park. J.T.P. is a Beatriu de Pinós fellow (DEiU, Generalitat de Catalunya).

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Núria Bayó-Puxan
    • 1
  • Ariadna Fernández
    • 1
  • Judit Tulla-Puche
    • 1
  • Estela Riego
    • 1
  • Mercedes Álvarez
    • 1
    • 2
  • Fernando Albericio
    • 1
    • 3
  1. 1.Institute for Research in BiomedicineBarcelona Science Park, University of BarcelonaBarcelonaSpain
  2. 2.Laboratory of Organic Chemistry, Faculty of PharmacyUniversity of BarcelonaBarcelonaSpain
  3. 3.Department of Organic ChemistryUniversity of BarcelonaBarcelonaSpain

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