Synthesis of human growth hormone-releasing hormone via three-fragment serine/threonine ligation (STL)

Org Biomol Chem. 2013 Sep 14;11(34):5584-7. doi: 10.1039/c3ob41027g.

Abstract

The synthesis of human growth hormone-releasing hormone (hGH-RH), by the chemoselective serine/threonine ligations (STLs) of three unprotected peptide fragments, is reported. To allow for the multiple-fragment ligation, we chose the Msz (p-(methylsulfinyl)benzyloxycarbonyl) group, which is compatible with the preparation of peptide salicylaldehyde esters via Fmoc-SPPS and readily removed by reductive acidolysis, to protect the serine and threonine residue at the N-terminus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Growth Hormone-Releasing Hormone / chemical synthesis*
  • Growth Hormone-Releasing Hormone / chemistry
  • Humans
  • Molecular Structure
  • Peptide Fragments / chemistry*
  • Serine / chemistry*
  • Threonine / chemistry*

Substances

  • Peptide Fragments
  • Threonine
  • Serine
  • Growth Hormone-Releasing Hormone