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Cyclo(-arginyl-sarcosyl-aspartyl-phenylglycyl-)2. Simple synthesis of an RGD-related peptide with inhibitory activity for platelet aggregation

DOI: 10.1039/p19960000939

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 939 - 946 (1996)

Update date:2022-09-26

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Authors:

Nishino, NorikazuNishino, Norikazu

Hayashida, JunHayashida, Jun

Arai, ToruArai, Toru

Mihara, HisakazuMihara, Hisakazu

Ueno, YukioUeno, Yukio

Kumagai, HiromichiKumagai, Hiromichi

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Article abstract of DOI:10.1039/p19960000939

The dimerization-cleavage of the tetrapeptide precursor bound to the benzophenone oxime resin afforded cyclo[-Arg(Tos)-Sar-Asp(OcHex)-Phg-]2, a cyclic analogue of the RGD peptide. The yield and the selectivity between the tetra-/octa-peptide formed through the cyclization-cleavage depended on the sequence of the tetrapeptide. The ratio of tetra-/octa-peptide also depended on the substitution level of the oxime resin with the peptide segment. The cyclic octapeptide was also synthesized through the solution-phase dimerization-cyclization from the linear tetrapeptide precursor. The solution-phase dimerization-cyclization was very efficiently mediated with BOP/HOBt as the condensation reagent. 1H NMR and CD spectra suggested that the cyclic octapeptide was of some restricted conformation, which might be involved in the preferred formation of the octapeptide in both solid- and solution-phase syntheses. The octapeptide showed potent inhibitory activity toward platelet aggregation; however, it showed no activity toward cell adhesion.

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Product name:(S)-N-{(S)-[(S)-4-({Amino-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-1-(benzyloxycarbonylmethyl-methyl-carbamoyl)-butylcarbamoyl]-phenyl-methyl}-3-tert-butoxycarbonylamino-succinamic acid cyclohexyl ester

Cas No:146878-13-9

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