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Solid-Phase synthesis of peptide nucleic acids

✍ Scribed by Dr. Leif Christensen; Richard Fitzpatrick; Brian Gildea; Kenneth H. Petersen; Henrik F. Hansen; Troels Koch; Michael Egholm; Ole Buchardt; Peter E. Nielsen; Dr. James Coull; Rolf H. Berg

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 638 KB
Volume: 1
Category: Article
ISSN: 1075-2617
DOI: 10.1002/psc.310010304

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✦ Synopsis

Peptide nucleic acids (PNA) were synthesized by a modified Merrifield method using several improvements. Activation by O-[benzotriazol-1-yl]-1,1,3,3-tetramethyluronium hexafluorophosphate in combination with in situ neutralization of the resin allowed efficient coupling of all four Boc-protected PNA monomers within 30 min. HPLC analysis of the crude product obtained from a fully automated synthesis of the model PNA oligomer H-CGGACTAAGTCCATTGC-Gly-NH2, indicated an average yield per synthetic cycle of 97.1%. N1-benzyloxycarbonyl-N6(3)-methylimidazole triflate substantially outperformed acetic anhydride as a capping reagent. The resin-bound PNAs were successfully cleaved by the 'low-high' trifluoromethanesulphonic acid procedure.

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