A highly efficient in situ N-acetylation approach for solid phase synthesis

2014 ◽  
Vol 12 (12) ◽  
pp. 1879-1884 ◽  
Author(s):  
Koushik Chandra ◽  
Tapta Kanchan Roy ◽  
Johnny N. Naoum ◽  
Chaim Gilon ◽  
R. Benny Gerber ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Highly Efficient

In situ peptide acetylation.

scholarly journals Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

2013 ◽  
Vol 9 ◽  
pp. 2395-2403 ◽  
Author(s):  
Felix Wojcik ◽  
Sinaida Lel ◽  
Alexander G O’Brien ◽  
Peter H Seeberger ◽  
Laura Hartmann
Keyword(s):  
Double Bond ◽  
Building Block ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis ◽  
Highly Efficient ◽  
Monomer Sequence ◽  
Full Control ◽  
Block Approach

We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key step to prepare these building blocks suitable for fully automated solid-phase synthesis. Introduction of the sugar ligands via functionalized building blocks rather than postfunctionalization of the oligomeric backbone allows for the straightforward synthesis of multivalent glycoligands with full control over monomer sequence and functionalization pattern. We demonstrate the potential of this building-block approach by synthesizing oligomers with different numbers and spacing of carbohydrates and also show the feasibility of heteromultivalent glycosylation patterns by combining building blocks presenting different mono- and disaccharides.

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