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Anthelmintic PF1022A: stepwise solid-phase synthesis of a cyclodepsipeptide containing N-methyl amino acids
research-article
16 December 2011
ACN, acetonitrile,
Boc, tert-butyloxycarbonyl,
BOPCl, N,N′-bis(2-oxo-3-oxazolidinyl)phosphinic chloride,
DCM, dichloromethane,
DEAD, diethylazodicarboxylate,
DHP, 3,4-dihydro-2H-pyrane,
DIC, N,N′-diisopropylcarbodiimide,
DIEA, diisopropylethylamine,
DMAP, 4-dimethylaminopyridine,
DMF, dimethylformamide,
DMSO, dimethylsulfoxide,
EDCI, 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide methiodide,
Fmoc, 9-Fluorenyl-methoxycarbonyl,
HATU, N,N,N′,N′-tetramethyl-O-(7-azabenzo-triazol-1-yl)uroniumhexa-fluorophosphate,
HOAt, 1-hydroxy-7-azabenzotriazole,
HOBt, 1-hydroxy-benzotriazole,
MeOH, methanol,
TEA, triethylamine,
TFA, trifluoro acetic acid,
THF, tetrahydrofuran,
THP, tetrahydropyranyl,
TPP, triphenylphosphane,
p-TsOH, para-toluenesulfonic acid
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Abstract
Cyclodepsipeptides of the enniation-, PF1022-, and verticilide-family represent a diverse class of highly interesting natural products with respect to their manifold biological activities. However, until now no stepwise solid-phase synthesis has been accomplished due to the difficult combination of N-methyl amino acids and hydroxycarboxylic acids. We report here the first stepwise solid-phase synthesis of the anthelmintic cyclooctadepsipeptide PF1022A based on an Fmoc/THP-ether protecting group strategy on Wang-resin. The standard conditions of our synthesis allow an unproblematic adaption to an automated peptide synthesizer.
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acn, acetonitrile,boc, tert-butyloxycarbonyl,bopcl, n,n′-bis(2-oxo-3-oxazolidinyl)phosphinic chloride,dcm, dichloromethane,dead, diethylazodicarboxylate,dhp, 3,4-dihydro-2h-pyrane,dic, n,n′-diisopropylcarbodiimide,diea, diisopropylethylamine,dmap, 4-dimethylaminopyridine,dmf, dimethylformamide,dmso, dimethylsulfoxide,edci, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide,fmoc, 9-fluorenyl-methoxycarbonyl,hatu, n,n,n′,n′-tetramethyl-o-(7-azabenzo-triazol-1-yl)uroniumhexa-fluorophosphate,hoat, 1-hydroxy-7-azabenzotriazole,hobt, 1-hydroxy-benzotriazole,meoh, methanol,tea, triethylamine,tfa, trifluoro acetic acid,thf, tetrahydrofuran,thp, tetrahydropyranyl,tpp, triphenylphosphane,p-tsoh, para-toluenesulfonic acid
acn, acetonitrile, boc, tert-butyloxycarbonyl, bopcl, n,n′-bis(2-oxo-3-oxazolidinyl)phosphinic chloride, dcm, dichloromethane, dead, diethylazodicarboxylate, dhp, 3,4-dihydro-2h-pyrane, dic, n,n′-diisopropylcarbodiimide, diea, diisopropylethylamine, dmap, 4-dimethylaminopyridine, dmf, dimethylformamide, dmso, dimethylsulfoxide, edci, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide, fmoc, 9-fluorenyl-methoxycarbonyl, hatu, n,n,n′,n′-tetramethyl-o-(7-azabenzo-triazol-1-yl)uroniumhexa-fluorophosphate, hoat, 1-hydroxy-7-azabenzotriazole, hobt, 1-hydroxy-benzotriazole, meoh, methanol, tea, triethylamine, tfa, trifluoro acetic acid, thf, tetrahydrofuran, thp, tetrahydropyranyl, tpp, triphenylphosphane, p-tsoh, para-toluenesulfonic acid