Amino acid derived 1,4-dialkyl substituted imidazolones

Frederik Diness; Morten Peter Meldal

doi:10.1002/bip.21359

Amino acid derived 1,4-dialkyl substituted imidazolones

5 Citations (Scopus)

Abstract

A general method for synthesis of 1,4-substituted imidazolones from amino acids on solid support or in solution has been developed. Amino acid derived 3-Boc-(1,3)-oxazinane (Box) protected amino aldehyde building blocks were coupled through urea bonds to the amino terminal of dipeptides or amino acids. Upon acidic release, the aldehyde instantaneously formed the cyclic N-carbamyliminium ion, which rearranged to the corresponding imidazolone. Under strongly acidic conditions the imidazolones acted as nuclophiles in the Pictet-Spengler reaction.

Original language	English
Journal	Biopolymers
Volume	94
Issue number	2
Pages (from-to)	236-241
ISSN	0006-3525
DOIs	https://doi.org/10.1002/bip.21359
Publication status	Published - 11 Mar 2010

Keywords

Amino Acids
Catalysis
Copper
Imidazoles
Molecular Structure
Former Faculty of Pharmaceutical Sciences

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10.1002/bip.21359

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title = "Amino acid derived 1,4-dialkyl substituted imidazolones",

abstract = "A general method for synthesis of 1,4-substituted imidazolones from amino acids on solid support or in solution has been developed. Amino acid derived 3-Boc-(1,3)-oxazinane (Box) protected amino aldehyde building blocks were coupled through urea bonds to the amino terminal of dipeptides or amino acids. Upon acidic release, the aldehyde instantaneously formed the cyclic N-carbamyliminium ion, which rearranged to the corresponding imidazolone. Under strongly acidic conditions the imidazolones acted as nuclophiles in the Pictet-Spengler reaction.",

keywords = "Amino Acids, Catalysis, Copper, Imidazoles, Molecular Structure, Former Faculty of Pharmaceutical Sciences",

author = "Frederik Diness and Meldal, {Morten Peter}",

note = "Keywords: amino acids, imidazolones, urea bonds, N-acyliminum, Pictet-Spengler reaction",

year = "2010",

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doi = "10.1002/bip.21359",

language = "English",

volume = "94",

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journal = "Biopolymers",

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T1 - Amino acid derived 1,4-dialkyl substituted imidazolones

AU - Diness, Frederik

AU - Meldal, Morten Peter

N1 - Keywords: amino acids, imidazolones, urea bonds, N-acyliminum, Pictet-Spengler reaction

PY - 2010/3/11

Y1 - 2010/3/11

N2 - A general method for synthesis of 1,4-substituted imidazolones from amino acids on solid support or in solution has been developed. Amino acid derived 3-Boc-(1,3)-oxazinane (Box) protected amino aldehyde building blocks were coupled through urea bonds to the amino terminal of dipeptides or amino acids. Upon acidic release, the aldehyde instantaneously formed the cyclic N-carbamyliminium ion, which rearranged to the corresponding imidazolone. Under strongly acidic conditions the imidazolones acted as nuclophiles in the Pictet-Spengler reaction.

AB - A general method for synthesis of 1,4-substituted imidazolones from amino acids on solid support or in solution has been developed. Amino acid derived 3-Boc-(1,3)-oxazinane (Box) protected amino aldehyde building blocks were coupled through urea bonds to the amino terminal of dipeptides or amino acids. Upon acidic release, the aldehyde instantaneously formed the cyclic N-carbamyliminium ion, which rearranged to the corresponding imidazolone. Under strongly acidic conditions the imidazolones acted as nuclophiles in the Pictet-Spengler reaction.

KW - Amino Acids

KW - Catalysis

KW - Copper

KW - Imidazoles

KW - Molecular Structure

KW - Former Faculty of Pharmaceutical Sciences

U2 - 10.1002/bip.21359

DO - 10.1002/bip.21359

M3 - Journal article

C2 - 20225297

SN - 0006-3525

VL - 94

SP - 236

EP - 241

JO - Biopolymers

JF - Biopolymers

IS - 2

ER -

Amino acid derived 1,4-dialkyl substituted imidazolones

Abstract

Keywords

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