Solid phase peptide synthesis. I. A mild method of solid phase peptide synthesis employing an enamine nitrogen protecting group and a benzhydryl resin as a solid support.

Southard, G.L.; Brooke, G. S.; Pettee, J. M.

doi:10.1016/s0040-4039(01)88433-1

Cited by 17 publications

(2 citation statements)

References 14 publications

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“…Initial preparation was by reduction of the ketone with sodium borohydride or sodium bis(2-methoxyethoxy)aluminum hydride;25 treatment of the resulting carbinol with HBr in methylene chloride gave the benzhydryl bromide polymer essentially as outlined by Southard and coworkers. 26 The desired amine derivative was obtained by treatment with ammonia in methylene chloride. The amine content was determined by titration as described by Dorman,27 by substitution with an amino acid and subsequent hydrolysis and amino acid analysis, or by the procedure of Esko.28…”

Section: Resultsmentioning

confidence: 99%

Preparation and use of benzhydrylamine polymers in peptide synthesis. II. Synthesis of thyrotropin releasing hormone, thyrocalcitonin 26-32, and eledoisin

Pietta¹,

Cavallo²,

Takahashi³

et al. 1974

J. Org. Chem.

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Three procedures have been developed for the synthesis of a benzhydrylamine polymer for the preparation of C-terminal amide peptides by solid-phase synthesis. From a common keto intermediate, prepared by acylation of polysterene-1% divinylbenzene with benzoyl chloride, the desired product can be obtained directly by the Leukart reaction, by reduction of an oxime intermediate, or by ammonolysis of the benzhydryl bromide intermediate. The application of this support to the syntheses of the wide range of peptide hormones possessing a C-terminal amide is illustrated by the syntheses of TRH, the C-terminal heptapeptide fragment of thyrocalcitonin, and the endecapeptide, eledoisin.

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Section: Resultsmentioning

confidence: 99%

Preparation and use of benzhydrylamine polymers in peptide synthesis. II. Synthesis of thyrotropin releasing hormone, thyrocalcitonin 26-32, and eledoisin

Pietta¹,

Cavallo²,

Takahashi³

et al. 1974

J. Org. Chem.

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“…Acidification of the salts to generate free carboxylic acids is difficult due to high acid sensitivity of the group. However, the Tfa analogs (R ¼ CF 3 ) can be isolated as free acids by acidification [33]. The N a -Mbv group can be removed by treatment with dilute AcOH or 0.4 M HCl in THF or 0.…”

Section: Benzhydryl Groupsmentioning

confidence: 99%