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. 1974 Dec;71(12):4945–4949. doi: 10.1073/pnas.71.12.4945

Synthesis of a Pentekontapeptide with High Lipolytic Activity Corresponding to the Carboxyl-Terminal Fifty Amino Acids of Ovine β-Lipotropin

Donald Yamashiro 1, Choh Hao Li 1
PMCID: PMC434016  PMID: 4531028

Abstract

The synthesis of a peptide, composed of fifty amino-acid residues, corresponding to positions 42-91 in ovine β-lipotropin has been accomplished by the solidphase method. The preformed symmetrical anhydride and active ester coupling methods were used exclusively. The synthetic product was purified by gel filtration, carboxymethylcellulose chromatography, and partition chromatography on Sephadex G-50. Its lipolytic activity in isolated rabbit fat cells was about six times that of β-lipotropin on a weight basis.

Keywords: anterior pituitary hormone, solid-phase method, rabbit fat cells

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Selected References

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  1. BIRK Y., LI C. H. ISOLATION AND PROPERTIES OF A NEW, BIOLOGICALLY ACTIVE PEPTIDE FROM SHEEP PITUITARY GLANDS. J Biol Chem. 1964 Apr;239:1048–1052. [PubMed] [Google Scholar]
  2. Chrétien M., Gilardeau C. Les lipotropines (LPH) hypophysaires. Union Med Can. 1973 Apr;102(4):890–898. [PubMed] [Google Scholar]
  3. Chrétien M., Gilardeau C., Li C. H. Revised structure of sheep beta-lipotropic hormone. Int J Pept Protein Res. 1972;4(4):263–265. doi: 10.1111/j.1399-3011.1972.tb03427.x. [DOI] [PubMed] [Google Scholar]
  4. Chrétien M., Li C. H. Isolation, purification, and characterization of gamma-lipotropic hormone from sheep pituitary glands. Can J Biochem. 1967 Jul;45(7):1163–1174. doi: 10.1139/o67-133. [DOI] [PubMed] [Google Scholar]
  5. Cseh G., Gráf L., Góth E. Lipotropic hormone obtained from human pituitary gland. FEBS Lett. 1968 Nov;2(1):42–44. doi: 10.1016/0014-5793(68)80096-1. [DOI] [PubMed] [Google Scholar]
  6. Gilardeau C., Chrétien M. Isolation and characterization of beta-lipolytic hormone from porcine pituitary gland. Can J Biochem. 1970 Sep;48(9):1017–1021. doi: 10.1139/o70-159. [DOI] [PubMed] [Google Scholar]
  7. Gisin B. F. The monitoring of reactions in solid-phase peptide synthesis with picric acid. Anal Chim Acta. 1972 Jan;58(1):248–249. doi: 10.1016/S0003-2670(00)86882-8. [DOI] [PubMed] [Google Scholar]
  8. Gráf L., Cseh G., Medzihradszky-Schweiger Isolation of gamma-lipotropic hormone from porcine pituitary glands. Biochim Biophys Acta. 1969 Mar;175(2):444–447. doi: 10.1016/0005-2795(69)90027-0. [DOI] [PubMed] [Google Scholar]
  9. Gráf L., Li C. H. Action of plasmin on ovine beta-lipotropin: revision of the carboxyl terminal sequence. Biochem Biophys Res Commun. 1973 Aug 21;53(4):1304–1309. doi: 10.1016/0006-291x(73)90607-4. [DOI] [PubMed] [Google Scholar]
  10. Gutte B., Merrifield R. B. The total synthesis of an enzyme with ribonuclease A activity. J Am Chem Soc. 1969 Jan 15;91(2):501–502. doi: 10.1021/ja01030a050. [DOI] [PubMed] [Google Scholar]
  11. Hagenmaier H., Frank H. Increased coupling yields in solid phase peptide synthesis with a modified carbodiimide coupling procedure. Hoppe Seylers Z Physiol Chem. 1972 Dec;353(12):1973–1976. [PubMed] [Google Scholar]
  12. LI C. H. LIPOTROPIN, A NEW ACTIVE PEPTIDE FROM PITUITARY GLANDS. Nature. 1964 Feb 29;201:924–924. doi: 10.1038/201924a0. [DOI] [PubMed] [Google Scholar]
  13. Lenard J., Robinson A. B. Use of hydrogen fluoride in Merrifield solid-phase peptide synthesis. J Am Chem Soc. 1967 Jan 4;89(1):181–182. doi: 10.1021/ja00977a057. [DOI] [PubMed] [Google Scholar]
  14. Loffet A. Improvement to the esterification procedure used in solid phase peptide synthesis. Int J Protein Res. 1971;3(5):297–299. doi: 10.1111/j.1399-3011.1971.tb01723.x. [DOI] [PubMed] [Google Scholar]
  15. Lohmar P., Li C. H. Biological proprtie of ovine beta-lipotropic hormone. Endocrinology. 1968 May;82(5):898–904. doi: 10.1210/endo-82-5-898. [DOI] [PubMed] [Google Scholar]
  16. Lohmar P., Li C. H. Isolation of bovine beta-lipotropic hormone. Biochim Biophys Acta. 1967 Oct 23;147(2):381–383. doi: 10.1016/0005-2795(67)90416-3. [DOI] [PubMed] [Google Scholar]
  17. MERRIFIELD R. B. SOLID-PHASE PEPTIDE SYNTHESIS. 3. AN IMPROVED SYNTHESIS OF BRADYKININ. Biochemistry. 1964 Sep;3:1385–1390. doi: 10.1021/bi00897a032. [DOI] [PubMed] [Google Scholar]
  18. Mazur R. H., Plume G. Improved synthesis of bradykinin. Experientia. 1968 Jul 15;24(7):661–661. doi: 10.1007/BF02138296. [DOI] [PubMed] [Google Scholar]
  19. Moon H. D., Li C. H., Jennings B. M. Immunohistochemical and histochemical studies of pituitary beta-lipotrophs. Anat Rec. 1973 Mar;175(3):529–537. doi: 10.1002/ar.1091750303. [DOI] [PubMed] [Google Scholar]
  20. Pankov Iu A., Iudaev N. A. Polnaia posledovatel'nost' aminokislotnykh ostatkov v molekule svinogo beta-lipotropina. Biokhimiia. 1972 Sep-Oct;37(5):991–1004. [PubMed] [Google Scholar]
  21. RODBELL M. METABOLISM OF ISOLATED FAT CELLS. I. EFFECTS OF HORMONES ON GLUCOSE METABOLISM AND LIPOLYSIS. J Biol Chem. 1964 Feb;239:375–380. [PubMed] [Google Scholar]
  22. Sajgó C., Gráf L., Barát E., Sajgó M. Amino acid sequence of porcine beta-lipotropic hormone. Biochim Biophys Acta. 1971 Jan 19;229(1):276–278. doi: 10.1016/0005-2795(71)90344-8. [DOI] [PubMed] [Google Scholar]
  23. Sakakibara S., Shimonishi Y., Kishida Y., Okada M., Sugihara H. Use of anhydrous hydrogen fluoride in peptide synthesis. I. Behavior of various protective groups in anhydrous hydrogen fluoride. Bull Chem Soc Jpn. 1967 Sep;40(9):2164–2167. doi: 10.1246/bcsj.40.2164. [DOI] [PubMed] [Google Scholar]
  24. Scott A. P., Lowry P. J. Adrenocorticotrophic and melanocyte-stimulating peptides in the human pituitary. Biochem J. 1974 Jun;139(3):593–602. doi: 10.1042/bj1390593. [DOI] [PMC free article] [PubMed] [Google Scholar]
  25. VAUGHAN M. The production and release of glycerol by adipose tissue incubated in vitro. J Biol Chem. 1962 Nov;237:3354–3358. [PubMed] [Google Scholar]
  26. Yamashiro D., Blake J., Li C. H. The use of N a , N im -Bis(tert-butyloxycarbonyl)histidine and N a -2-(p-biphenylyl)isopropyloxycarbonyl-N im -tert-butyloxy-carbonylhistidine in the solid-phase synthesis of histidine-containing peptides. J Am Chem Soc. 1972 Apr 19;94(8):2855–2859. doi: 10.1021/ja00763a053. [DOI] [PubMed] [Google Scholar]
  27. Yamashiro D., Li C. H. Adrenocorticotropins. 44. Total synthesis of the human hormone by the solid-phase method. J Am Chem Soc. 1973 Feb 21;95(4):1310–1315. doi: 10.1021/ja00785a049. [DOI] [PubMed] [Google Scholar]
  28. Yamashiro D., Li C. H. Protection of tryptophan with the formyl group in peptide synthesis. J Org Chem. 1973 Jul 27;38(15):2594–2597. doi: 10.1021/jo00955a004. [DOI] [PubMed] [Google Scholar]
  29. Yamashiro D., Li C. H. Protection of tyrosine in solid-phase peptide synthesis. J Org Chem. 1973 Feb 9;38(3):591–592. doi: 10.1021/jo00943a039. [DOI] [PubMed] [Google Scholar]

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