Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

Thomas Hjelmgaard; Sophie Faure; Dan Stærk; Claude Taillefumier; John Nielsen

doi:10.1039/c1ob05729d

Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

Thomas Hjelmgaard, Sophie Faure, Dan Stærk, Claude Taillefumier, John Nielsen

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Abstract

The development of a highly efficient methodology for solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) with free acids or free amides at the C-terminus is described. The arylopeptoids were synthesised by means of a convenient submonomer protocol in which the arylopeptoid residues were created in an iterative manner on the growing chain using an acylation-substitution cycle. The uronium salt COMU was found to be the most efficient reagent for ensuring fast and clean couplings of the benzoic acid building blocks.

Original language	English
Journal	Organic & Biomolecular Chemistry
Volume	9
Pages (from-to)	6832-6843
Number of pages	12
ISSN	1477-0520
DOIs	https://doi.org/10.1039/c1ob05729d
Publication status	Published - 7 Oct 2011

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10.1039/c1ob05729d

OrgBiomolChem2011 9 6832 6843Submitted manuscript, 533 KB

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abstract = "The development of a highly efficient methodology for solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) with free acids or free amides at the C-terminus is described. The arylopeptoids were synthesised by means of a convenient submonomer protocol in which the arylopeptoid residues were created in an iterative manner on the growing chain using an acylation-substitution cycle. The uronium salt COMU was found to be the most efficient reagent for ensuring fast and clean couplings of the benzoic acid building blocks.",

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T1 - Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

AU - Hjelmgaard, Thomas

AU - Faure, Sophie

AU - Stærk, Dan

AU - Taillefumier, Claude

AU - Nielsen, John

PY - 2011/10/7

Y1 - 2011/10/7

N2 - The development of a highly efficient methodology for solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) with free acids or free amides at the C-terminus is described. The arylopeptoids were synthesised by means of a convenient submonomer protocol in which the arylopeptoid residues were created in an iterative manner on the growing chain using an acylation-substitution cycle. The uronium salt COMU was found to be the most efficient reagent for ensuring fast and clean couplings of the benzoic acid building blocks.

AB - The development of a highly efficient methodology for solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) with free acids or free amides at the C-terminus is described. The arylopeptoids were synthesised by means of a convenient submonomer protocol in which the arylopeptoid residues were created in an iterative manner on the growing chain using an acylation-substitution cycle. The uronium salt COMU was found to be the most efficient reagent for ensuring fast and clean couplings of the benzoic acid building blocks.

U2 - 10.1039/c1ob05729d

DO - 10.1039/c1ob05729d

M3 - Journal article

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SN - 1477-0520

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JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

ER -

Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

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