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Chemical synthesis of an O-phosphorylated tyrosine analogue of human angiotensin II, -4 angiotensin II, and its vasoconstrictor effect in intact sheep


, : Chemical synthesis of an O-phosphorylated tyrosine analogue of human angiotensin II, -4 angiotensin II, and its vasoconstrictor effect in intact sheep. Peptide Research 6(4): 205-210

The derivative N-alpha-fluorenylmethoxycarbonyl-O-dimethylphosphono-L-tyrosine was utilized in continuous-flow solid-phase synthesis to prepare the O-phosphotyrosine analogue of human angiotensin II, (Tyr(P)-4) angiotensin II. Side-chain deprotection, including the removal of the methyl phosphate groups, as well as cleavage of the peptide from the solid support was achieved with 1 M trimethylsilylbromide-thioanisole in trifluoroacetic acid. Overall yield of purified peptide was 46%. The pressor response in intact sheep to graded infusions of the synthetic (Tyr(P)-4) angiotensin II showed it to have similar potency to the native angiotensin II. However, a prolonged, elevated mean arterial pressure was observed following cessation of the infusion.

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PMID: 8400616


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