Amino acid derived 1,4-dialkyl substituted imidazolones

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Amino acid derived 1,4-dialkyl substituted imidazolones. / Diness, Frederik; Meldal, Morten Peter.

I: Biopolymers, Bind 94, Nr. 2, 11.03.2010, s. 236-241.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Harvard

Diness, F & Meldal, MP 2010, 'Amino acid derived 1,4-dialkyl substituted imidazolones', Biopolymers, bind 94, nr. 2, s. 236-241. https://doi.org/10.1002/bip.21359

APA

Diness, F., & Meldal, M. P. (2010). Amino acid derived 1,4-dialkyl substituted imidazolones. Biopolymers, 94(2), 236-241. https://doi.org/10.1002/bip.21359

Vancouver

Diness F, Meldal MP. Amino acid derived 1,4-dialkyl substituted imidazolones. Biopolymers. 2010 mar 11;94(2):236-241. https://doi.org/10.1002/bip.21359

Author

Diness, Frederik ; Meldal, Morten Peter. / Amino acid derived 1,4-dialkyl substituted imidazolones. I: Biopolymers. 2010 ; Bind 94, Nr. 2. s. 236-241.

Bibtex

@article{3016dbe0ee814ff397bac3efacf624fd,
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 = "3",
day = "11",
doi = "10.1002/bip.21359",
language = "English",
volume = "94",
pages = "236--241",
journal = "Biopolymers",
issn = "0006-3525",
publisher = "Wiley",
number = "2",

}

RIS

TY - JOUR

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

VL - 94

SP - 236

EP - 241

JO - Biopolymers

JF - Biopolymers

SN - 0006-3525

IS - 2

ER -

ID: 34206032