Journal of Organic Chemistry p. 1664 - 1668 (1989)
Update date:2022-09-26
Topics:
Guillaume, Helen A.
Perich, John W.
Johns, R. B.
Tregear, Geoffrey W.
The first synthesis of the N(1)-(dimethylphosphono)tryptophan derivatives Z-Trp(PO3Me2)-OBzl and Boc-Trp(PO3Me2)-ONBzl by reaction of the lithium indolate of protected tryptophan derivatives Z-Trp-OBzl and Boc-Trp-ONBzl with dimethyl phosphorochloridate is described.The N(1)-(dimethylphosphono)tryptophan or Trp(Dmop) derivatives are stable to hydrogenation, and to TFA and high HF treatment, and can be fully deprotected with TFMSA/TFA/m-cresol/dimethyl sulfide or TFMSA/TFA/m-cresol/thioanisole to yield the novel hydrophilic amino acid N(1)-phosphonotryptophan quantitatively.Weak base treatment of Trp(Dmop) compounds yields N(1)-(methylphosphono)tryptophan derivatives.
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