Transcription of Amine Protecting Groups: Carboxylic Acid …
1 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.
2 Alanine (ala or A)chiralOHNH2OR = i-Pr; valine (val or V)chiralCH3H3 COHNH2OR = i-Bu; leucine (Leu or L)chiralCH3H3 COHNH2OR = s-Bu; isoleucine (Ile or I)chiralCH3CH3 The L- amino Acids: with alcohol functionalityOHNH2OR = HOCH2; serine (ser or S)chiralOHNH2O; threonine (Thr or T)chiralOHH3 CHOThe L- amino Acids: with sulfur functionalityOHNH2OR = HSCH2; cycteine (cys or C)chiralOHNH2O; methionine (met or M)chiralHSSH3 CThe L- amino Acids: with carboxylate functionalityOHNH2O; aspartate (asp or D) or aspartic acidchiralHO2 COHNH2O; glutamate (glu or E) or glutamic acidchiralHO2 CThe L- amino Acids: with amide functionalityOHNH2O; asparagine (asn or N)chiralOHNH2O; glutamine (gln or Q)chiralOH2 NOH2 NThe L- amino Acids: with basic Amine functionalityOHNH2O lysine (lys or K)chiralNH2 OHNH2 Oarginine (Arg or R)chiralNHH2 NNHThe L- amino Acids: witharomactic ringsOHNH2OR = Ph; phenylalanine (phe or F)chiralOHNH2OR = p-OH-Ph; tyrosine (tyr or Y)chiralHOThe L- amino Acids: with nitrogenhetreocyclic ringsOHNHO; proline (pro or P)chiralOHNH2OR = imid; histidine (his or H)chiralNNHOHNH2OR = indole.
3 Tryptophan (trp or W)chiralNHThe L- amino Acids:ROHNH2 ORONH3 OHOHNH2OR = H; glycine (gly or G)achiralThe L- amino Acids: with aliphatic side chainH3 COHNH2OR = CH3; alanine (ala or A)chiralOHNH2OR = i-Pr; valine (val or V)chiralCH3H3 COHNH2OR = i-Bu; leucine (Leu or L)chiralCH3H3 COHNH2OR = s-Bu; isoleucine (Ile or I)chiralCH3CH3 The L- amino Acids: with alcohol functionalityOHNH2OR = HOCH2; serine (ser or S)chiralOHNH2O; threonine (Thr or T)chiralOHH3 CHOThe L- amino Acids: with sulfur functionalityOHNH2OR = HSCH2; cycteine (cys or C)chiralOHNH2O; methionine (met or M)chiralHSSH3 CThe L- amino Acids: with carboxylate functionalityOHNH2O; aspartate (asp or D) or aspartic acidchiralHO2 COHNH2O; glutamate (glu or E) or glutamic acidchiralHO2 CThe L- amino Acids: with amide functionalityOHNH2O; asparagine (asn or N)chiralOHNH2O; glutamine (gln or Q) or glutamic acidchiralOH2 NOH2 NThe L- amino Acids: with basic Amine functionalityOHNH2O lysine (lys or K)chiralNH2 OHNH2 Oarginine (Arg or R)chiralNHH2 NNHThe L- amino Acids: witharomactic ringsOHNH2OR = Ph; phenylalanine (phe or F)chiralOHNH2OR = p-OH-Ph.
4 Tyrosine (tyr or Y)chiralHOThe L- amino Acids: with nitrogenhetreocyclic ringsOHNHO; proline (pro or P)chiralOHNH2OR = imid; histidine (his or H)chiralNNHOHNH2OR = indole; tryptophan (trp or W)chiralNHThe L- amino Acids:ROHNH2 ORONH3 OHOHNH2OR = H; glycine (gly or G)achiralThe L- amino Acids: with aliphatic side chainH3 COHNH2OR = CH3; alanine (ala or A)chiralOHNH2OR = i-Pr; valine (val or V)chiralCH3H3 COHNH2OR = i-Bu; leucine (Leu or L)chiralCH3H3 COHNH2OR = s-Bu; isoleucine (Ile or I)chiralCH3CH3 The L- amino Acids: with alcohol functionalityOHNH2OR = HOCH2; serine (ser or S)chiralOHNH2O; threonine (Thr or T)chiralOHH3 CHOThe L- amino Acids: with sulfur functionalityOHNH2OR = HSCH2; cycteine (cys or C)chiralOHNH2O; methionine (met or M)chiralHSSH3 CThe L- amino Acids: with carboxylate functionalityOHNH2O; aspartate (asp or D) or aspartic acidchiralHO2 COHNH2O; glutamate (glu or E) or glutamic acidchiralHO2 CThe L- amino Acids: with amide functionalityOHNH2O; asparagine (asn or N)chiralOHNH2O.
5 Glutamine (gln or Q) or glutamic acidchiralOH2 NOH2 NThe L- amino Acids: with basic Amine functionalityOHNH2O lysine (lys or K)chiralNH2 OHNH2 Oarginine (Arg or R)chiralNHH2 NNHThe L- amino Acids: witharomactic ringsOHNH2OR = Ph; phenylalanine (phe or F)chiralOHNH2OR = p-OH-Ph; tyrosine (tyr or Y)chiralHOThe L- amino Acids: with nitrogenhetreocyclic ringsOHNHO; proline (pro or P)chiralOHNH2OR = imid; histidine (his or H)chiralNNHOHNH2OR = indole; tryptophan (trp or W)chiralNHThe D- amino Acids:ROHNH2 ORONH3 OROHNH2 ORONH3 ONCNDCC =OOOOO(Boc)O2 =Boc =OOOClOCbzCl =Cbz =OO
