Literature DB >> 6270658

New segment-coupling method for peptide synthesis in aqueous solution: application to synthesis of human [Gly17]-beta-endorphin.

J Blake, C H Li.   

Abstract

The thiolcarboxyl peptide [17-thiolglycine]-beta-endorphin-(1-17) (I) was synthesized by the solid-phase method. Reaction of peptide I with citraconic anhydride gave citraconyl-[Lys(Cit9,GlyS17]-beta-endorphin-(1-17) (Ia). Peptide Ia was coupled to another synthetic peptide, [Lys(Cit)19,24,28,29]-beta-endorphin-(18-31), by reaction with silver nitrate--N-hydroxysuccinimide in water. All citraconyl groups were removed in aqueous acetic acid, and [Gly17]-beta-endorphin was isolated in 30-40% yield. The synthetic analog had 10% analgesic potency and 59% opiate--receptor binding activity when compared with human beta-endorphin.

Entities:  

Mesh：

Substances：

Year:  1981        PMID： 6270658      PMCID： PMC319724          DOI： 10.1073/pnas.78.7.4055

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  9 in total

1.  PARTITION CHROMATOGRAPHY OF OXYTOCIN ON 'SEPHADEX'.

Authors:  D YAMASHIRO
Journal:  Nature       Date:  1964-01-04       Impact factor: 49.962

2.  beta-Endorphin: characteristics of binding sites in the rat brain.

Authors:  P Ferrara; R Houghten; C H Li
Journal:  Biochem Biophys Res Commun       Date:  1979-08-13       Impact factor: 3.575

3.  Activity of bovine pancreatic deoxyribonuclease A with modified amino groups.

Authors:  B V Plapp; S Moore; W H Stein
Journal:  J Biol Chem       Date:  1971-02-25       Impact factor: 5.157

4.  Reversible blocking of amino groups with citraconic anhydride.

Authors:  H B Dixon; R N Perham
Journal:  Biochem J       Date:  1968-09       Impact factor: 3.857

5.  Synthesis and analgesic activity of human beta-endorphin analogs substituted at positions 17, 18, or 19.

Authors:  J Blake; L F Tseng; C H Li
Journal:  Int J Pept Protein Res       Date:  1980-02

6.  The purification of peptides by partition chromatography based on a hydrophobicity scale.

Authors:  D Yamashiro
Journal:  Int J Pept Protein Res       Date:  1979-01

7.  beta-Endorphin: complete primary structure is required for full analgesic activity.

Authors:  C H Li; L F Tseng; D Yamashiro
Journal:  Biochem Biophys Res Commun       Date:  1978-11-29       Impact factor: 3.575

8.  Preparation and properties of Nalpha-9-fluorenylmethyloxycarbonylamino acids bearing tert.-butyl side chain protection.

Authors:  C D Chang; M Waki; M Ahmad; J Meienhofer; E O Lundell; J D Haug
Journal:  Int J Pept Protein Res       Date:  1980-01

9.  Peptide segment coupling in aqueous medium: silver ion activation of the thiolcarboxyl group.

Authors:  J Blake
Journal:  Int J Pept Protein Res       Date:  1981-02
  9 in total
  12 in total

1.  Total synthesis of the large non-ribosomal peptide polytheonamide B.

Authors:  Masayuki Inoue; Naoki Shinohara; Shintaro Tanabe; Tomoaki Takahashi; Ken Okura; Hiroaki Itoh; Yuki Mizoguchi; Maiko Iida; Nayoung Lee; Shigeru Matsuoka
Journal:  Nat Chem       Date:  2010-02-21       Impact factor: 24.427

2.  Promising general solution to the problem of ligating peptides and glycopeptides.

Authors:  Ping Wang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-11-04       Impact factor: 15.419

Review 3.  Contemporary strategies for peptide macrocyclization.

Authors:  Christopher J White; Andrei K Yudin
Journal:  Nat Chem       Date:  2011-06-23       Impact factor: 24.427

4.  Peptide segment ligation strategy without use of protecting groups.

Authors:  C F Liu; J P Tam
Journal:  Proc Natl Acad Sci U S A       Date:  1994-07-05       Impact factor: 11.205

5.  Total synthesis of human beta-lipotropin.

Authors:  J Blake; C H Li
Journal:  Proc Natl Acad Sci U S A       Date:  1983-03       Impact factor: 11.205

6.  Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides.

Authors:  Andrew G Roberts; Eric V Johnston; Jae-Hung Shieh; Joseph P Sondey; Ronald C Hendrickson; Malcolm A S Moore; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2015-10-01       Impact factor: 15.419

7.  Toward Homogeneous Erythropoietin: Application of Metal Free Dethiylation in the Chemical Synthesis of the Ala79-Arg166 Glycopeptide Domain.

Authors:  Suwei Dong; Shiying Shang; Zhongping Tan; Samuel J Danishefsky
Journal:  Isr J Chem       Date:  2011-11       Impact factor: 3.333

8.  Synthesis of O-Sulfated Human Syndecan-1-like Glyco-polypeptides by Incorporating Peptide Ligation and O-Sulfated Glycopeptide Cassette Strategies.

Authors:  Tianlu Li; Weizhun Yang; Sherif Ramadan; Xuefei Huang
Journal:  Org Lett       Date:  2020-08-06       Impact factor: 6.005

9.  Topological mapping of acetylcholine receptor: evidence for a model with five transmembrane segments and a cytoplasmic COOH-terminal peptide.

Authors:  E F Young; E Ralston; J Blake; J Ramachandran; Z W Hall; R M Stroud
Journal:  Proc Natl Acad Sci U S A       Date:  1985-01       Impact factor: 11.205

10.  Toward homogeneous erythropoietin: non-NCL-based chemical synthesis of the Gln78-Arg166 glycopeptide domain.

Authors:  Zhongping Tan; Shiying Shang; Tamara Halkina; Yu Yuan; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-04-22       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.