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Stereoselective Synthesis of Ψ[CH2O] Pseudodipeptides and Conformational Analysis of a PheΨ[CH2O]Ala Containing Analogue of the Drug Desmopressin
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
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2002 (English)In: Bioorganic & Medicinal Chemistry Letters, Vol. 12, no 6, 841-4 p.Article in journal (Refereed) Published
Abstract [en]

A method for synthesis of XaaΨ[CH2O]Ala/Gly pseudodipeptides in good yields and excellent diastereoselectivity from azido alcohols and (R)-2-chloropropionic acid or tert-butyl bromoacetate has been developed. Insertion of one of the pseudodipeptide building blocks in the peptide drug desmopressin revealed that methylene ether isosteres may have only a minor influence on the secondary structure of peptides.

Place, publisher, year, edition, pages
2002. Vol. 12, no 6, 841-4 p.
Identifiers
URN: urn:nbn:se:umu:diva-9094DOI: doi:10.1016/S0960-894X(02)00016-1OAI: oai:DiVA.org:umu-9094DiVA: diva2:148765
Available from: 2008-02-29 Created: 2008-02-29 Last updated: 2011-01-13Bibliographically approved

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Hedenström, MattiasKihlberg, Jan
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