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Pentaerythrityltetramine scaffolds for solid-phase combinatorial chemistry.
MedLine Citation:
PMID:  15058947     Owner:  NLM     Status:  MEDLINE    
Straightforward synthesis for two pentaerythrityltetramine precursors, 2,2-bis(azidomethyl)propane-1,3-diamine (1) and 2-[N-(allyloxycarbonyl)aminomethyl]-2-azidomethylpropane-1,3-diamine (2), has been described. Both propane-1,3-diamines have been attached by reductive amination to a solid-supported backbone amide linker derived from 4-(4-formyl-3,5-dimethoxyphenoxy)butyric acid. The presence of the two methoxy substituents on the linker is essential to avoid cross-linking between two linkers. The remaining free primary amino group of the propane-1,3-diamine moiety may then be selectively acylated with an appropriately protected amino acid using conventional N,N-dicyclohexylcarbodiimide/1-hydroxybenzotriazole (DCC/HOBt) activation without any interference by the secondary amino function. The latter group may be subsequently acylated by an anhydride method. Sequential reduction of the azido group and removal of the allyloxycarbonyl protection from 2 allow further coupling of two different amino acids, and hence, this handle may be utilized in construction of branched structures containing four different amino acids or peptides. Solid-supported 1 may, in turn, be used for the synthesis of similar constructs containing two identical branches. It is worth noting that no acid-labile protecting groups are required in this approach, and hence, this dimension may be saved for the cleavage of the linker. The applicability of the scaffolds to library synthesis has been demonstrated by preparation of 11 pentaerythrityl-branched tetra- and octapeptides.
Pasi Virta; Marika Leppänen; Harri Lönnberg
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Mar 
Date Detail:
Created Date:  2004-04-02     Completed Date:  2004-05-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2008-16     Citation Subset:  IM    
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.
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MeSH Terms
Amines / chemistry*
Amino Acids / chemistry
Chromatography, High Pressure Liquid
Combinatorial Chemistry Techniques
Heterocyclic Compounds / chemical synthesis*
Molecular Structure
Oligopeptides / chemical synthesis
Propylene Glycols / chemistry*
Reg. No./Substance:
0/Amines; 0/Amino Acids; 0/Heterocyclic Compounds; 0/Oligopeptides; 0/Propylene Glycols; 115-77-5/pentaerythritol

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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