A Simple & Convenient Solid Phase Synthesis of Bacterial Origin Octapeptide Sequence, Glu-Asp-Gly-Asn-Lys-Pro-Gly-Lys-OH

The repeating octapeptide sequence, Glu-Asp-Gly-Asn-Lys-Pro-Gly-Lys-OH derived from the glycoprotein found in Staphylococcus aureus cell wall is assembled by simple solid phase peptide synthesis methodology using a base labile linker

On the Peptides of l-Lysine

By carbobenzoxylation of Nϵ-monobenzylidene-l-lysine (I) followed by acidification benzaldehyde is split off and pure α-monocarbobenzoxy-l-lysine (IIIa) is formed. By the action of dry hydrogen bromide dissolved in glacial acetic acid on Nϵ-trityl-Nα-carbobenzoxy-l-lysine methyl ester only the carbobenzoxy group is eliminated and crystalline dihydrobromide of pure Nϵ-trityl-l-lysine methyl ester (V) is formed; on treatment of Nα,Nϵ-ditrityl-l-lysine methyl ester with two equivalents of hydrogen chloride in methanol only the Nα-trityl group is split off and the crystalline dihydrochloride of the same Nα-trityl derivative V is formed. Compounds III and V are valuable intermediates for the preparation of different types of lysine peptides, III for the synthesis of ϵ-peptides and V for the synthesis of α-as well as mixed α,ϵ-peptides of lysine. Several such peptides were prepared in this way. © 1961, American Chemical Society. All rights reserved