Solid-phase synthesis of peptide nucleic acids

R Fitzpatrick; B Gildea; O Buchardt; J Coull; Peter E. Nielsen

doi:10.1002/psc.310010304

Solid-phase synthesis of peptide nucleic acids

R Fitzpatrick, B Gildea, O Buchardt, J Coull, Peter E. Nielsen

Abstract

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.

Originalsprog	Engelsk
Tidsskrift	Journal of Peptide Science
Vol/bind	1
Udgave nummer	3
Sider (fra-til)	175-83
Antal sider	9
ISSN	1075-2617
DOI	https://doi.org/10.1002/psc.310010304
Status	Udgivet - 1 maj 1995

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10.1002/psc.310010304

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title = "Solid-phase synthesis of peptide nucleic acids",

abstract = "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.",

keywords = "Base Sequence, Chromatography, High Pressure Liquid, Indicators and Reagents, Methods, Molecular Structure, Nucleic Acids/chemical synthesis, Peptides/chemical synthesis, Resins, Synthetic, Solvents",

author = "R Fitzpatrick and B Gildea and O Buchardt and J Coull and Nielsen, {Peter E.}",

year = "1995",

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doi = "10.1002/psc.310010304",

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TY - JOUR

T1 - Solid-phase synthesis of peptide nucleic acids

AU - Fitzpatrick, R

AU - Gildea, B

AU - Buchardt, O

AU - Coull, J

AU - Nielsen, Peter E.

PY - 1995/5/1

Y1 - 1995/5/1

N2 - 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.

AB - 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.

KW - Base Sequence

KW - Chromatography, High Pressure Liquid

KW - Indicators and Reagents

KW - Methods

KW - Molecular Structure

KW - Nucleic Acids/chemical synthesis

KW - Peptides/chemical synthesis

KW - Resins, Synthetic

KW - Solvents

U2 - 10.1002/psc.310010304

DO - 10.1002/psc.310010304

M3 - Journal article

C2 - 9222994

SN - 1075-2617

VL - 1

SP - 175

EP - 183

JO - Journal of Peptide Science

JF - Journal of Peptide Science

IS - 3

ER -

Solid-phase synthesis of peptide nucleic acids

Abstract

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