| Polymeric and dendrimeric pyridoxal enzyme mimics. | |
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MedLine Citation:
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PMID: 15158796 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Pyridoxal was covalently attached to polyethylenimine polymers, but the resulting materials were found to degrade rapidly. In comparison, the dendrimeric pyridoxals, which possess only one pyridoxal unit at the core of every dendrimer molecule were found to be relatively stable compounds. A total of 12 poly(amidoamine) type dendrimers were synthesized. They range from G1 to G6 with either NMe(2) or NHAc termini. The NMe(2)-terminated pyridoxal dendrimers racemize alpha-amino acids 50-100 times faster than does simple pyridoxal, while the NHAc-terminated pyridoxal dendrimers racemize alpha-amino acids only 3-5 times faster than does simple pyridoxal. Both the NMe(2)- and NHAc-terminated pyridoxal dendrimers decarboxylate 2-amino-2-phenyl-propionic acid 1-3 times faster than simple pyridoxal. The interior polarity in the pyridoxal dendrimers is similar to that of 85:15 water-DMF solution. Furthermore, we successfully incorporated eight lauryl groups to the G5 pyridoxal dendrimer at known positions. The laurylated dendrimer exhibits lower racemization and decarboxylation rates than do the unlaurylated ones, in contrast to the positive rate effects of laurylation in polyethylenimine-pyridoxamines in our previous transamination studies. |
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Authors:
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Lei Liu; Ronald Breslow |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 12 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2004 Jun |
Date Detail:
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Created Date: 2004-05-25 Completed Date: 2005-01-31 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 3277-87 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Columbia University, New York, NY 10027, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemistry Biomimetic Materials / chemical synthesis, chemistry* Catalysis Decarboxylation Enzymes / chemistry*, metabolism* Kinetics Models, Molecular Molecular Conformation Molecular Structure Polyethyleneimine / chemical synthesis, chemistry* Pyridoxal / chemical synthesis, chemistry* Spectrum Analysis |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Enzymes; 66-72-8/Pyridoxal; 9002-98-6/Polyethyleneimine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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