Transcription of Protecting Groups (PG) - ETH Zürich
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Protecting Groups (PG) - ETH Zürich
Protecting Groups (PG)General Considerations Avoid undesired side reaction PGs have to be Easily introduced and safely removed Stable in reaction conditions Orthogonal Which Groups need protection?If R contains NH2, OH, SH, COOH or other reactive functionalitiesReview: Albericio et al., Chem. Rev., 2009, 109, 24552 Amine PGsMost commonIntroductionFmoc ClBoc2 ORemovalPiperidineTFAS tableAcidic conditions, HydrogenationBasic conditions, HydrogenationOrthogonalBoc, Z, Trt, AllocFmoc, Z, Trt, Alloc3 amino Acids: LysineOther Protecting group : BocAmine PGsIntroduction Cbz2O, Cbz ClAlloc2O, Alloc ClivDde OHRemovalH2Pd(PPh3), PhSiH32% N2H4 StableBasic and Acidic conditionsBasic and Acidic conditionsBasic and Acidic conditions, HydrogenationOrthogonal Boc, Fmoc, TrtBoc, Fmoc, TrtBoc, Fmoc, Z, Trt, Alloc4 For carboxylic acids, Aspartic and Glutamic AcidCarboxylic acid PGsIntroductionIsobuteneTrt ClDmb OH,Dmb ClFm OHBn Cl, Bn2 ORemoval90%
Protecting Groups (PG) General Considerations • Avoid undesired side reaction ... For α‐carboxylic acids, Aspartic and Glutamic Acid Carboxylic acid PGs Introduction Isobutene Trt‐Cl Dmb‐OH, ... Amino Acids: Cysteine Other protecting group: Trt
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PROTECTING GROUPS, Acid, Amino Groups, Amino, Coupling Reagents, Amino acid, Amino protecting groups, ORTHOGONALITY OF PROTECTING GROUPS, Protecting, Groups, Solid Phase Peptide Synthesis, Strategies and Resins, Methods in Peptide Synthesis. Part, Amino Acid-Protecting Groups, Protecting Groups Handout A