Suppression of Diketopiperazine Formation in Solid Phase Peptide Synthesis

When N-methylmorpholine salt of Boc-Ile was coupled with HCl·Pro-Pro-resin suspended in methylenechloride by dicyclohexylcarbodiimide, diketopiperazine formation of the dipeptide-resin was suppressed almost completely and the isoleucine residue in the synthesized Boc-Ile-Pro-Pro-resin was not racemi...

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Published inChemical & pharmaceutical bulletin Vol. 23; no. 1; pp. 222 - 224
Main Authors SUZUKI, KENJI, NITTA, KAZUO, ENDO, NOBUYOSHI
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 01.01.1975
Japan Science and Technology Agency
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ISSN0009-2363
1347-5223
DOI10.1248/cpb.23.222

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Summary:When N-methylmorpholine salt of Boc-Ile was coupled with HCl·Pro-Pro-resin suspended in methylenechloride by dicyclohexylcarbodiimide, diketopiperazine formation of the dipeptide-resin was suppressed almost completely and the isoleucine residue in the synthesized Boc-Ile-Pro-Pro-resin was not racemized. Generalization of this coupling procedure in a schedule for solid phase peptide synthesis is suggested.
Bibliography:ObjectType-Article-1
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.23.222