- Synthesis of autophagosomal marker protein LC3-II under detergent-free conditions
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Just add oil: A new detergent-free method was developed to synthesize lipidated proteins using a light-activatable solubilizing side chain (in dashed circle, see scheme) to assist the ligation of the lipopeptides. This method allows the efficient preparation of a phosphatidylethanolamine-conjugated autophagosomal marker protein (LC3-II) as well as labeled derivatives of LC3-II, which can be used to study autophagy regulation. Copyright
- Huang, Yi-Chao,Li, Yi-Ming,Chen, Yang,Pan, Man,Li, Yi-Tong,Yu, Li,Guo, Qing-Xiang,Liu, Lei
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- General Fmoc-Based Solid-Phase Synthesis of Complex Depsipeptides Circumventing Problematic Fmoc Removal
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Development of an Fmoc-based solid-phase depsipeptide methodology has been hampered by base-promoted fragmentation and diketoperazine formation upon Fmoc group elimination. Such a strategy would be a useful tool given the number of commercially available Fmoc-protected residues. Herein we report that the addition of small percentages of organic acids to the Fmoc-removal cocktail proves effective to circumvent these drawbacks and most importantly, allowed the development of an exclusively solid-phase stepwise methodology to prepare a highly complex depsipeptide with multiple and consecutive esters bonds. Alongside, the optimal protecting group scheme for residue incorporation, which is not as straightforward as it is for traditional peptide synthesis, was explored. The developed stepwise strategy proved effective for the synthesis of a highly complex cyclodepsipeptide, being comparable to the yields obtained when using traditional combined chemistry approaches.
- Lobo-Ruiz, Ariadna,Tulla-Puche, Judit
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supporting information
p. 183 - 192
(2020/01/24)
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- Synthesis of N-protected N-methyl serine and threonine
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Two efficient and convenient syntheses of N-Cbz and N-Fmoc N-methyl serine and threonine are described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone.
- Luo, Yue,Evindar, Ghotas,Fishlock, Dan,Lajoie, Gilles A
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p. 3807 - 3809
(2007/10/03)
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- Mild, selective cleavage of amino acid and peptide β-(trimethylsilyl)ethoxymethyl (SEM) esters by magnesium bromide
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Magnesium bromide etherate has been previously shown to cleave β-(trimethylsilyl)ethoxymethyl (SEM) esters of aliphatic acids. This methodology has now been extended to amino acid and peptide derivatives in the presence of protecting groups typically encountered in peptide chemistry, including the Boc, Cbz, Fmoc and Troc carbamates as well as benzyl-, tert-butyl- and tert-butyldimethylsilyl ethers. The stability of fluoride sensitive protecting groups to magnesium bromide allows for added selectivity in the removal of SEM esters in organic synthesis.
- Chen, Wei-Chuan,Vera, Matthew D.,Joullie, Madeleine M.
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p. 4025 - 4028
(2007/10/03)
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- Application of t-Butyldimethylsilyl Ethers of Serine, Threonine and Tyrosine in Peptide Synthesis
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The utility of Tbdms (t-butyldimethylsilyl) ethers, prepared conveniently in a one pot procedure from Nα-Fmoc (9-fluorenylmethoxycarbonyl) and Nα-Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives.The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains assembly, desirable, e.g., for phosphorylation of glycosylation.
- Fischer, Peter M.
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p. 7605 - 7608
(2007/10/02)
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