Application of a photolabile backbone amide linker for cleavage of internal amides in the synthesis towards melanocortin subtype-4 agonists
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Application of a photolabile backbone amide linker for cleavage of internal amides in the synthesis towards melanocortin subtype-4 agonists. / Minkwitz, Rolf; Meldal, Morten.
I: QSAR and Combinatorial Science, Bind 24, Nr. 3, 04.2005, s. 343-353.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Application of a photolabile backbone amide linker for cleavage of internal amides in the synthesis towards melanocortin subtype-4 agonists
AU - Minkwitz, Rolf
AU - Meldal, Morten
PY - 2005/4
Y1 - 2005/4
N2 - A new photolabile backbone amide handle has been developed for the synthesis of a melanocortin subtype-4 receptor (MCR4) agonist library in the solid phase. This traceless linker allows for the solid-supported synthesis of internal amides and their release under very mild, orthogonal conditions from solid support. The chemistry to attach an amide onto the linker is discussed. Structural variations of the linker in order to facilitate the attachment are investigated. The cleavage rate on the solid phase was measured. Finally, a small arylpiperazine library towards the MCR4 receptor was synthesized and its members characterized via HPLC, MS and NMR.
AB - A new photolabile backbone amide handle has been developed for the synthesis of a melanocortin subtype-4 receptor (MCR4) agonist library in the solid phase. This traceless linker allows for the solid-supported synthesis of internal amides and their release under very mild, orthogonal conditions from solid support. The chemistry to attach an amide onto the linker is discussed. Structural variations of the linker in order to facilitate the attachment are investigated. The cleavage rate on the solid phase was measured. Finally, a small arylpiperazine library towards the MCR4 receptor was synthesized and its members characterized via HPLC, MS and NMR.
KW - Combinatorial chemistry
KW - Handles
KW - Libraries
KW - Linkers
KW - Solid-phase synthesis
UR - http://www.scopus.com/inward/record.url?scp=18344365619&partnerID=8YFLogxK
U2 - 10.1002/qsar.200420050
DO - 10.1002/qsar.200420050
M3 - Journal article
AN - SCOPUS:18344365619
VL - 24
SP - 343
EP - 353
JO - Molecular Informatics
JF - Molecular Informatics
SN - 1868-1743
IS - 3
ER -
ID: 326847434