Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity
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Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity. / Laursen, Jane B.; De Visser, Peter C.; Nielsen, Henrik K.; Jensen, Knud J.; Nielsen, John.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 12, No. 2, 21.01.2002, p. 171-175.Research output: Contribution to journal › Journal article › peer-review
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TY - JOUR
T1 - Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity
AU - Laursen, Jane B.
AU - De Visser, Peter C.
AU - Nielsen, Henrik K.
AU - Jensen, Knud J.
AU - Nielsen, John
PY - 2002/1/21
Y1 - 2002/1/21
N2 - An array of 12 new saphenamycin analogues modified at the benzoate moiety was synthesized on solid support. Synthesis commenced with a chemoselective anchoring of saphenic acid through the carboxyl group to a 2-chlorotrityl functionalized polystyrene resin. The secondary alcohol was acylated in parallel with a series of differently substituted benzoic acid derivatives. Treatment with TFA-CH2Cl2 (5:995) released the expected saphenamycin analogues into solution. These new analogues were purified, characterized and screened for antimicrobial activity against Bacillus subtilis and Proteus mirabilis. Eight analogues exhibited MIC values against B. subtilis ranging from 0.07 to 3.93 μg/mL, comparable to the activities of previously reported saphenamycin analogues.
AB - An array of 12 new saphenamycin analogues modified at the benzoate moiety was synthesized on solid support. Synthesis commenced with a chemoselective anchoring of saphenic acid through the carboxyl group to a 2-chlorotrityl functionalized polystyrene resin. The secondary alcohol was acylated in parallel with a series of differently substituted benzoic acid derivatives. Treatment with TFA-CH2Cl2 (5:995) released the expected saphenamycin analogues into solution. These new analogues were purified, characterized and screened for antimicrobial activity against Bacillus subtilis and Proteus mirabilis. Eight analogues exhibited MIC values against B. subtilis ranging from 0.07 to 3.93 μg/mL, comparable to the activities of previously reported saphenamycin analogues.
U2 - 10.1016/S0960-894X(01)00692-8
DO - 10.1016/S0960-894X(01)00692-8
M3 - Journal article
C2 - 11755347
AN - SCOPUS:0037147788
VL - 12
SP - 171
EP - 175
JO - Bioorganic & Medicinal Chemistry Letters
JF - Bioorganic & Medicinal Chemistry Letters
SN - 0960-894X
IS - 2
ER -
ID: 129206953