Solid-phase synthesis of rigid acylpolyamines using temporary N-4,4'-dimethoxytrityl protection in the presence of trityl linkers
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Solid-phase synthesis of rigid acylpolyamines using temporary N-4,4'-dimethoxytrityl protection in the presence of trityl linkers. / Olsen, Christian A; Witt, Matthias; Jaroszewski, Jerzy W; Franzyk, Henrik.
In: Journal of Organic Chemistry, Vol. 69, No. 18, 2004, p. 6149-52.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Solid-phase synthesis of rigid acylpolyamines using temporary N-4,4'-dimethoxytrityl protection in the presence of trityl linkers
AU - Olsen, Christian A
AU - Witt, Matthias
AU - Jaroszewski, Jerzy W
AU - Franzyk, Henrik
PY - 2004
Y1 - 2004
N2 - An N-protection protocol employing the 4,4'-dimethoxytrityl (Dmt) group in combination with borane reduction of resin-bound polyamides was shown to be an efficient methodology that enables synthesis of novel analogues of natural acylpolyamine toxins. Thus, three philanthotoxins containing polyamine chains with piperidyl and cyclohexyl structural elements, which introduce conformational rigidity, increased lipophilicity, and altered proteolytic properties, were obtained in 39-44% overall yield.
AB - An N-protection protocol employing the 4,4'-dimethoxytrityl (Dmt) group in combination with borane reduction of resin-bound polyamides was shown to be an efficient methodology that enables synthesis of novel analogues of natural acylpolyamine toxins. Thus, three philanthotoxins containing polyamine chains with piperidyl and cyclohexyl structural elements, which introduce conformational rigidity, increased lipophilicity, and altered proteolytic properties, were obtained in 39-44% overall yield.
KW - Boranes
KW - Catalysis
KW - Molecular Structure
KW - Polyamines
KW - Structure-Activity Relationship
KW - Trityl Compounds
KW - Wasp Venoms
U2 - 10.1021/jo049278q
DO - 10.1021/jo049278q
M3 - Journal article
C2 - 15373506
VL - 69
SP - 6149
EP - 6152
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 18
ER -
ID: 42370567