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65949106377
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We have recently disclosed a sulfur ylide-based linker for the solid phase synthesis of C-terminal α-ketoacid peptides. While this protocol works well for many complex, unprotected peptides it is not appropriate for simpler ketoacids or for peptides with cysteine or methionine residues: Ju, L.; Bode, J. W. Org. Biomol. Chem. 2009, 7, 2259
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77951807253
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Note
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2O, rt). We do not detect the 2,5-dihydrooxazole 3-oxide as an intermediate.
-
-
-
-
21
-
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77951782027
-
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The use of additives such as Lewis acids or dehydrating reagents did not significantly improve yield
-
The use of additives such as Lewis acids or dehydrating reagents did not significantly improve yield.
-
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22
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77951846155
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24
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0017591592
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For similar deprotection conditions on a side-chain unprotected peptide, see
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For similar deprotection conditions on a side-chain unprotected peptide, see: Veber, D. F.; Paleveda, W. J., Jr.; Lee, Y. C.; Hirschmann, R. J. Org. Chem. 1977, 42, 3286-3288
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25
-
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77951870496
-
-
Note
-
Despite the ring-chain tautomerization, this α-ketoacid may be used for decarboxylative condensation with an N -alkylhydroxylamine. See Supporting Information.
-
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