Studies on peptides. CXXVII. Synthesis of a tripentacontapeptide with epidermal growth factor activity.

Akaji, Kenichi; Fujii, Nobutaka; Yajima, Haruaki; Hayashi, Kyozo; Mizuta, Kei; Aono, Mitsuru; Moriga, Motoyuki

doi:10.1248/cpb.33.184

Cited by 16 publications

(12 citation statements)

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“…Despite successful syntheses of the HIV-1 protease (22) and of a limited number of other proteins (30)(31)(32)(33)(34)(35), at the start of the decade of the 1990s total chemical synthesis, by the standard methods of peptide chemistry of even a small protein molecule remained a daunting task, often requiring large teams and taking years to complete, with no guarantee of success. The routine, reproducible preparation of synthetic polypeptides of defined chemical structure was limited to products of ∼50 amino acid residues (19; Figure 2).…”

Section: Synthetic-peptide Chemistry: Useful But Boundedmentioning

confidence: 99%

Synthesis of Native Proteins by Chemical Ligation

Dawson

Kent²

2000

Annu. Rev. Biochem.

1,582

1,526

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Key Words chemical protein synthesis, thioester, protein, peptide, solid phase synthesis, polymer-supported synthesis, protein engineering s Abstract In just a few short years, the chemical ligation of unprotected peptide segments in aqueous solution has established itself as the most practical method for the total synthesis of native proteins. A wide range of proteins has been prepared. These synthetic molecules have led to the elucidation of gene function, to the discovery of novel biology, and to the determination of new three-dimensional protein structures by both NMR and X-ray crystallography. The facile access to novel analogs provided by chemical protein synthesis has led to original insights into the molecular basis of protein function in a number of systems. Chemical protein synthesis has also enabled the systematic development of proteins with enhanced potency and specificity as candidate therapeutic agents.

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Section: Synthetic-peptide Chemistry: Useful But Boundedmentioning

confidence: 99%

Synthesis of Native Proteins by Chemical Ligation

Dawson

Kent²

2000

Annu. Rev. Biochem.

1,582

1,526

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“…The vasoactive angiotensin II (AII, DRVYIHPF) 15) and its [Gly 8 ]-AII analogue were selected. Although this cleavage procedure is used routinely at low temperature in solution synthesis, 16,17) we decided to compare the rate of peptide chain removal from a total of six peptidyl-resins at both 0°C and 25°C. Therefore, the main goal was to investigate the influence of different factors upon the efficacy of the TFMSA/TFA method.…”

mentioning

confidence: 99%

Evaluation of the Trifluoromethanosulfonic Acid/Trifluoroacetic Acid/Thioanisole Cleavage Procedure for Application in Solid-Phase Peptide Synthesis.

Jubilut

Cilli

Tominaga

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…There have been limited studies of the activities of synthetic peptide segments of EGF. Komoriya et al found that the linear and cyclic forms ofthe B-loop peptide (residues [20][21][22][23][24][25][26][27][28][29][30][31] were active in both receptor binding and biological stimulation in cell culture but to a very low extent (0.003% of EGF), while the other loops were inactive (7). On the basis of these data, they proposed that the B loop of EGF contains both the receptor-binding and biological-stimulation activities of the molecule.…”

mentioning

confidence: 99%

A synthetic approach to structure-function relationships in the murine epidermal growth factor molecule.

Heath¹,

Merrifield²

1986

Proc. Natl. Acad. Sci. U.S.A.

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A synthetic approach to structure-function relationships in the murine epidermal growth factor molecule (solid- Contributed by R. B. Merrifield, May 19, 1986 ABSTRACT Murine epidermal growth factor, a 53-amino acid peptide that is mitogenic for a number of cell types, has been synthesized by the solid-phase method. The synthetic peptide is identical to the natural material in amino acid composition, chromatographic behavior, receptor binding, and stimulation of DNA synthesis. Fragments of the EGF molecule corresponding to residues 42-53, 32-53, and 15-53 were constructed as well as the methionine sulfoxide derivative of EGF, [Met(0)21JEGF-(1-53), and a polymeric form of EGF.[Met(0)21]EGF-(1-53) was slightly less active than EGF in receptor binding and stimulation of DNA synthesis. Polymeric EGF was 1/100th as active as EGF, while EGF-(15-53) was less potent than EGF-(1-53) by a factor of 104. EGF-(32-53) was even less active and EGF-(43-53) was inactive.

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Studies on peptides. CXXVII. Synthesis of a tripentacontapeptide with epidermal growth factor activity.

Cited by 16 publications

References 1 publication

Synthesis of Native Proteins by Chemical Ligation

Synthesis of Native Proteins by Chemical Ligation

Evaluation of the Trifluoromethanosulfonic Acid/Trifluoroacetic Acid/Thioanisole Cleavage Procedure for Application in Solid-Phase Peptide Synthesis.

A synthetic approach to structure-function relationships in the murine epidermal growth factor molecule.

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