Journal article

SYNTHESIS OF AN N-1-PHOSPHOTRYPTOPHAN-CONTAINING TRIPEPTIDE - GLUTAMYL-N-1-PHOSPHOTRYPTOPHYLLEUCINE

HA GUILLAUME, JW PERICH, JD WADE, GW TREGEAR, RB JOHNS

JOURNAL OF ORGANIC CHEMISTRY | AMER CHEMICAL SOC | Published : 1989

Abstract

The novel protected amino acid Nα-(tert-buty1oxycarbony1)-N1-(dimethylphosphono)tryptophan or Boc-Trp(Dmop)-OH, was used in the solution-phase synthesis of the tripeptide Z-Glu(OBzl)-Trp(Dmop)-Leu-OBzl. The N1-phosphotryptophan-containing peptide H-Glu-Trp(PO3H2)-Leu-OH was obtained by the selective deprotection of the protected tripeptide with CF3SO3H/CF3CO2H / m-cresol/DMS or thioanisole. The dimethylphosphate group was also evaluated as a new protecting group for the tryptophan indole moiety and was found to effectively suppress tert-butylation of the indole ring during acidolytic removal of the Boc group and to be stable to “high” HF conditions, palladium-catalyzed hydrogenation, and CF3..

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