The Formation of Impossible Rings in Macrocyclooligomerizations for Cyclodepsipeptide Synthesis: The 18-from-12 Paradox.
The Formation of Impossible Rings in Macrocyclooligomerizations for Cyclodepsipeptide Synthesis: The 18-from-12 Paradox.
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DOI：
10.1021/acs.joc.0c03069
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发表时间：
2021-06-18
期刊：
影响因子：
--
通讯作者：
Johnston JN
中科院分区：
文献类型：
--
作者：
Smith AN;Johnston JN
A reinvestigation into the macrocyclooligomerization (MCO) of a tetradepsipeptide is reported, uncovering a paradox in which the MCO of depsipeptide monomers can produce “impossible” ring sizes: a 12-atom chain produced the expected 24-membered ring, alongside unexpected 18- and 30-membered cyclic oligomeric depsipeptides (CODs). We report an alternative preparation of authentic 18- and 36-membered macrocycles for this case using a stepwise synthesis that provides definitive analytical characterization for each ring size. Our investigation yields a recharacterization and reassignment of two macrocycles originally reported in this MCO series, along with updated yields and isothermal titration calorimetry data after implementation of new critical protocols for purification and subsequent analysis. Initial studies to probe this mechanistic conundrum are described.
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影响因子：
15
作者：
Evans, DA;Seidel, D;Downey, CW
通讯作者：
Downey, CW
影响因子：
3.9
作者：
Claveria-Gimeno, Rafael;Velazquez-Campoy, Adrian;Pey, Angel Luis
通讯作者：
Pey, Angel Luis
影响因子：
4.4
作者：
Darby, Samuel J.;Platts, Lauren;Falconer, Robert J.
通讯作者：
Falconer, Robert J.
DOI：
10.1139/v75-226
发表时间：
1975-01-01
期刊：
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
影响因子：
--
作者：
DESLONGCHAMPS, P;CHENEVERT, R;SAUNDERS, JK
通讯作者：
SAUNDERS, JK
影响因子：
2.1
作者：
Dudin, L;Pattenden, G;Wilson, C
通讯作者：
Wilson, C