Safe and efficient Boc-SPPS for the synthesis of glycopeptide-α- thioesters

Journal of Peptide Science

Volumn 20, Issue 2, 2014, Pages 98-101

  Izumi, Masayuki ^a   Murakami, Masumi ^a   Okamoto, Ryo ^a   Kajihara, Yasuhiro ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

glycopeptide thioester; oligosaccharide; safety Boc solid phase peptide synthesis; sialic acid; thiolysis

Indexed keywords

DIOXANE; FLUORIDE; GLYCOPEPTIDE; GLYCOPEPTIDE ALPHA THIOESTER; HYDROGEN; RESIN; SULFURIC ACID; THIOL; UNCLASSIFIED DRUG; ESTER; THIOL DERIVATIVE;

ACIDITY; ARTICLE; PRIORITY JOURNAL; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SOLID; ACYLATION; CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROCEDURES; SOLID PHASE SYNTHESIS; SYNTHESIS;

ACYLATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; GLYCOPEPTIDES; MOLECULAR STRUCTURE; SOLID-PHASE SYNTHESIS TECHNIQUES; SULFHYDRYL COMPOUNDS;

EID: 84892821545     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2608     Document Type: Article

References (10)

1. Dawson PE, Muir TW, Clark-Lewis I, Kent SBH,. Synthesis of proteins by native chemical ligation. Science 1994; 266: 776-779.
2. Hackenberger CP, Schwarzer D,. Chemoselective ligation and modification strategies for peptides and proteins. Angew. Chem. Int. Ed. Engl. 2008; 47: 10030-10074.
3. Kang J, Macmillan D,. Peptide and protein thioester synthesis via N -> S acyl transfer. Org. Biomol. Chem. 2010; 8: 1993-2002.
4. Schnölzer M, Alewood P, Jones A, Alewood D, Kent SBH,. In situ neutralization in boc-chemistry solid phase peptide synthesis-Rapid, high yield assembly of difficult sequences. Int. J. Pept. Res. Ther. 2007; 13: 31-44.
5. Murakami M, Okamoto R, Izumi M, Kajihara Y,. Chemical synthesis of an erythropoietin glycoform containing a complex-type disialyloligosaccharide. Angew. Chem. Int. Ed. 2012; 51: 3567-3572.
6. Yajima H, Fujii N,. Studies on Peptides. 103. Chemical synthesis of a crystalline protein with the full enzymatic-activity of Ribonuclease-A. J. Am. Chem. Soc. 1981; 103: 5867-5871.
7. Yajima H, Fujii N, Ogawa H, Kawatani H,. Trifluoromethanesulphonic acid, as a deprotecting reagent in peptide chemistry. J. Chem. Soc. Chem. Commun. 1974; (3): 107-108.
8. Makimura Y, Kiuchi T, Izumi M, Dedola S, Ito Y, Kajihara Y,. Efficient synthesis of glycopeptide-alpha-thioesters with a high-mannose type oligosaccharide by means of tert-Boc-solid phase peptide synthesis. Carbohydr. Res. 2012; 364: 41-48.
9. Houghten RA, Beckman A, Ostresh JM,. Use of 10-percent sulfuric acid/dioxane for removal of N-alpha-tertiary-butyloxycarbonyl group during solid-phase peptide-synthesis. Int. J. Pept. Prot. Res. 1986; 27: 653-658.
10. Gates ZP, Stephan JR, Lee DJ, Kent SBH,. Rapid formal hydrolysis of peptide-(alpha)thioesters. Chem. Commun. 2013; 49: 786-788.