title: Synthesis of granulocyte-macrophage colony-stimulating factor as homogeneous glycoforms and early comparisons with yeast cell-derived material.
abstract: Granulocyte-macrophage colony-stimulating factor (GM-CSF) is a medicinally important glycoprotein, used as an immunostimulant following bone-marrow transplant. On the basis of reports of its potential utility as an anticancer vaccine adjuvant, we undertook to develop a synthetic route toward single-glycoform GM-CSF. We describe herein a convergent total synthesis of GM-CSF aglycone and two homogeneous glycoforms. Analytical and biological studies confirm the structure and activity of these synthetic congeners.
authors: Laboratory for Bio-Organic Chemistry and Cell Biology Program, Sloan-Kettering Institute for Cancer Research, New York, NY 10065.
authors: Qiang
authors: Q
authors: Zhang
authors: Eric V
authors: EV
authors: Johnston
authors: Jae-Hung
authors: JH
authors: Shieh
authors: Malcolm A S
authors: MA
authors: Moore
authors: Samuel J
authors: SJ
authors: Danishefsky
mesh_terms: D000409:Alanine / Q000737:chemistry; D000595:Amino Acid Sequence; D003545:Cysteine / Q000737:chemistry; D004926:Escherichia coli; D006031:Glycosylation; D016178:Granulocyte-Macrophage Colony-Stimulating Factor / Q000138:chemical synthesis*; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011487:Protein Conformation
chemical_list: D016178:Granulocyte-Macrophage Colony-Stimulating Factor; D003545:Cysteine; D000409:Alanine
keywords: alanine ligation; glycoprotein synthesis; peptide ligation