Transcription of Amine Protecting Groups: Carboxylic Acid …
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Amine Protecting Groups: Carboxylic Acid …
The L- amino Acids:In contrast to the sugars the naturally occuring amino acids are occur in the L-configuration and not D- amino Acids:ROHNH2 ORONH3OH3 COHOHOD-lactic acidOHOHOD-glyceraldehydeOHPeptide Synthesis:peptides are oligo- or poly- amino acidsAmine Protecting Groups: Carboxylic acid Protecting Groups: ROHNH2 OROHNOHBoc(Boc)O2 TFAROHNH2O t-BuOH CO2 OOOOO(Boc)O2 =Boc =OOROHNH2 OROHNOHCbzCbzClH2Pd/CROHNH2 OOClOCbzCl =Cbz =OOROHNH2 OROt-BuNH2 OTFAROHNH2O t-BuOHH+H2Pd/CROHNH2 OROHNH2 OROBnNH2OK2CO3 BnBrR1 OHNOHBoc+R2 OBnNH2OH2Pd/CDCCR1 NNOHBocHOR2 OBnDCCR1 NNOHBocHOR2 OHR1 NNOHBocHOR2 OHR3Ot-BuNH2O+R1 NNOHBocHOR2 NHOOt-BuR3 TFAR1 NNOHHHOR2 NHOOHR3 t-BuOH CO2tri-peptide protected di-peptide protected tri-peptideSelectivedeprotection DCU DCU tolNCNDCC =NNOHHDCU =The L- amino Acids:ROHNH2 ORONH3 OHOHNH2OR = H; glycine (gly or G)achiralThe L- amino Acids: with aliphatic side chainH3 COHNH2OR = CH3.
peptides are oligo- or poly-amino acids Amine Protecting Groups: Carboxylic Acid Protecting Groups: R OH NH2 O R OH N O BocH (Boc)O2 TFA R OH NH2 – t-BuOH O – CO2 OOO OO (Boc)O2 = Boc= O O R OH NH2 O R OH N O CbzH CbzCl H2 Pd/C R OH NH2 O OCl O Cbzl= Cbz = O O R OH NH 2 O R Ot-Bu NH2 O TFA R OH NH2
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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