AminoAcidSynthesis - Amino acids and Proteins(Ch 21.2 21.8...

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Amino acids and Proteins (Ch. 21.2, 21.8, 23.3, 23.6, 15.8) : Laboratory Methods for Peptide Synthesis (a) Protection and deprotection steps for C-terminal end (the acid) “PROT C” and “dePROT C” C H 3 N H CH 2 Ph O OH C H 3 N H CH 3 O OH C H 2 N H CH 3 O OCH 3 CH 3 OH HCl C H 2 N H CH 3 O OCH 2 Ph C H 2 N H CH 3 O OC(CH 3 ) 3 HCl HCl (CH 3 ) 3 COH PhCH 2 OH C H 3 N H CH 3 O OH H 2 /Pd-C or HBr (anh);S N 2 HBr (anh);S N 2 CF 3 CO 2 H Cl O OCH 2 Ph N 3 O OC(CH 3 ) 3 BocN 3 C N H H CH 2 Ph O OH O PhH 2 CO C N H H CH 2 Ph O OH O (H 3 C) 3 CO CF 3 CO 2 H S N 1 H 2 /Pd-C or HBr (anh);S N 2 C H 3 N H CH 2 Ph O OH Phe Phe CBzPhe BocPhe Ala Ala CBzCl AlaOtBu AlaOMe AlaOBn O O N 3 FmocN 3 C N H H CH 2 Ph O OH O O FmocPhe S N 1 NH E1cb GOAL: Preparation of a tripeptide - Ala-Val-Gly (see pKa table for structures); one plan might be this: C H 3 N H CH 3 O C H N H CH(CH 3 ) 2 O C H N H H O OH Ala-Val-Gly PROT-Ala-Val-Gly-PROT DCC PROT-Ala-Val + Gly-PROT dePROT N Ala dePROT C Gly Gly PROT Gly C dePROT C Val PROT-Ala-Val-PROT DCC
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