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 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Biopolymers
Vol/bind	94
Udgave nummer	2
Sider (fra-til)	236-241
ISSN	0006-3525
DOI	https://doi.org/10.1002/bip.21359
Status	Udgivet - 11 mar. 2010

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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",

month = mar,

day = "11",

doi = "10.1002/bip.21359",

language = "English",

volume = "94",

pages = "236--241",

journal = "Biopolymers",

issn = "0006-3525",

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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

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