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 ClBoc2ORemovalPiperidineTFAStableAcidic conditions, HydrogenationBasic conditions, HydrogenationOrthogonalBoc, Z, Trt, AllocFmoc, Z, Trt, Alloc3Amino Acids: LysineOther Protecting group : BocAmine PGsIntroduction Cbz2O, Cbz ClAlloc2O, Alloc ClivDde OHRemovalH2Pd(PPh3), PhSiH32% N2H4StableBasic and Acidic conditionsBasic and Acidic conditionsBasic and Acidic conditions, HydrogenationOrthogonal Boc, Fmoc, TrtBoc, Fmoc, TrtBoc, Fmoc, Z, Trt, Alloc4For carboxylic acids, Aspartic and Glutamic AcidCarboxylic acid PGsIntroductionIsobuteneTrt ClDmb OH,Dmb ClFm OHBn Cl, Bn2ORemoval90% TFA 1
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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Acid, Amino acid, PROTECTING GROUPS, Amino Acid-Protecting Groups, Protecting, Amino, Coupling Reagents, Amino protecting groups, ORTHOGONALITY OF PROTECTING GROUPS, Groups, Amino Groups, Methods in Peptide Synthesis. Part, Protecting Groups Handout A, Solid Phase Peptide Synthesis, Strategies and Resins