J. Morley
1966
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Abstract
Publisher Summary This chapter discusses the synthesis of O-peptides of tyrosine, serine, and threonine. Various peptides containing O-lysyl-tyrosine, -serine, and -threonine residues are prepared by condensing Nα-t-butyloxycarbonyl (=BOC)-Nɛ-benzyloxycarbonyl (=Z)-lysine with the appropriately N-protected hydroxyamino-acid esters or amides; mild acid hydrolysis of the products yields O-(Nɛ-Z-lysyl) derivatives of the protected hydroxyamino-acid esters or amides, from which peptides are built up from the Nα-position by usual methods. Alternatively, Nα-Z-Nɛ-BOC-lysine gives O-(Nα-Z-lysyl) derivatives of the protected hydroxyamino-acid esters or amides, from which peptides are built up from the N*-position. Pyridine is used extensively in carbodi-imide coupling reactions with acetone or acetonitrile as solvent. High yields of O-(Nα- or Nɛ-Z-lysyl)-tyrosine and -serine derivatives, and 50–60% yields of analogous threonine derivatives are thereby obtained. This method is applicable in the esterification of acylamino-acids and aromatic acids with phenols and primary or secondary alcohols but fails with tertiary alcohols.