Publication:

Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons

Date

Date

Date
2006
Journal Article
Published version

Citations

Citation copied

Stamm, S., & Heimgartner, H. (2006). Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons. Helvetica Chimica Acta, 89(9), 1841–1855. https://doi.org/10.1002/hlca.200690178

Abstract

Abstract

Abstract

The syntheses of phenacyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate and allyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate are reported. Reactions of these 2H-azirin-3-amine derivatives with Z-protected amino acids have shown them to be suitable synthons for the Aib-Pro unit in peptide synthesis. After incorporation into the peptide by means of the 'azirine/oxazolone method', the C-termini of the resulting peptides were deprotected selectively with Zn in AcOH or by a mild Pd0-promoted procedure, respectively.

Additional indexing

Creators (Authors)

  • Stamm, S
    affiliation.icon.alt
  • Heimgartner, H
    affiliation.icon.alt

Journal/Series Title

Journal/Series Title

Journal/Series Title

Volume

Volume

Volume
89

Number

Number

Number
9

Page range/Item number

Page range/Item number

Page range/Item number
1841

Page end

Page end

Page end
1855

Item Type

Item Type

Item Type
Journal Article

Dewey Decimal Classifikation

Dewey Decimal Classifikation

Dewey Decimal Classifikation

Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis

Language

Language

Language
English

Publication date

Publication date

Publication date
2006

Date available

Date available

Date available
2011-12-06

Publisher

Publisher

Publisher

ISSN or e-ISSN

ISSN or e-ISSN

ISSN or e-ISSN
0018-019X

OA Status

OA Status

OA Status
Green

Citations

Citation copied

Stamm, S., & Heimgartner, H. (2006). Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons. Helvetica Chimica Acta, 89(9), 1841–1855. https://doi.org/10.1002/hlca.200690178

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Files
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