USE OF CYCLOPENTYL ESTER PROTECTION FOR ASPARTIC ACID TO REDUCE BASE CATALYZED SUCCINIMIDE FORMATION IN SOLID‐PHASE PEPTIDE SYNTHESIS

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Abstract
The effect of amino acid sequence and aspartyl protecting group on the rate of base catalyzed succinimide formation in the solid-phase synthesis of aspartyl peptides was studied. The peptides H-Ala-Asp-Gly-Phe-OH and H-Ala-Asp-Leu-Phe-OH were synthesized by the solid-phase method with cyclopentyl or benzyl protection for the .beta.-carboxyl of aspartic acid. The cyclopentyl ester was notably less susceptible to succinimide formation by treatment with tertiary amine than was the benzyl ester; the difference could have significant consequences for the synthesis of large peptides which contain reactive sequences such as Asp-Gly.