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Your search keyword '"El Oualid F"' showing total 3 results
Start Over Author "El Oualid F" Topic amino acids
3 results on '"El Oualid F"'

1. A practical synthesis of gramicidin s and sugar amino Acid containing analogues.

Author

Grotenbreg GM, Kronemeijer M, Timmer MS, El Oualid F, van Well RM, Verdoes M, Spalburg E, van Hooft PA, de Neeling AJ, Noort D, van Boom JH, van der Marel GA, Overkleeft HS, and Overhand M

Subjects
Amino Acids pharmacology, Anti-Bacterial Agents pharmacology, Bacillus cereus drug effects, Carbohydrates pharmacology, Enterococcus faecalis drug effects, Erythrocytes drug effects, Escherichia coli drug effects, Gramicidin pharmacology, Humans, Microbial Sensitivity Tests, Staphylococcus drug effects, Amino Acids chemical synthesis, Anti-Bacterial Agents chemical synthesis, Carbohydrates chemical synthesis, Gramicidin chemical synthesis
Abstract

A practical gram-scale and high-yielding synthesis of the antimicrobial peptide gramicidin S is presented. An Fmoc-based solid-phase peptide synthesis protocol is employed for the generation of the linear decapeptide precursor, which is cyclized in solution to afford the target compound. The versatility of our method is demonstrated by the construction of eight gramicidin S analogues (15a-h) having nonproteinogenic sugar amino acid residues (4-7) incorporated in the turn regions.

Published
2004
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2. Alkylated sugar amino acids: a new entry toward highly functionalized dipeptide isosters.

Author

Raunkjaer M, El Oualid F, van der Marel GA, Overkleeft HS, and Overhand M

Subjects
Catalysis, Cyclization, Dipeptides chemistry, Indicators and Reagents, Molecular Structure, Peptides, Cyclic chemistry, Stereoisomerism, Amino Acids chemistry, Dipeptides chemical synthesis, Peptides, Cyclic chemical synthesis, Sugar Acids chemistry
Abstract

[reaction: see text] Novel highly functionalized dipeptide isosters are synthesized via a diastereoselective alkyl/arylation protocol of a glucose-derived (R)-tert-butanesulfinylimine. One of these novel sugar amino acid derivatives, a D-Ala-Ser/Thr isostere, was applied in a peptide synthesis protocol to afford a cyclic tetramer.

Published
2004
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3. Design, synthesis, and evaluation of sugar amino acid based inhibitors of protein prenyl transferases PFT and PGGT-1.

Author

El Oualid F, Burm BE, Leroy IM, Cohen LH, van Boom JH, van den Elst H, Overkleeft HS, van der Marel GA, and Overhand M

Subjects
Alkyl and Aryl Transferases chemistry, Amino Acids chemistry, Amino Acids pharmacology, Animals, CHO Cells, Cell Line, Cricetinae, Drug Design, Farnesyltranstransferase, Structure-Activity Relationship, Sugar Acids chemistry, Sugar Acids pharmacology, Alkyl and Aryl Transferases antagonists & inhibitors, Amino Acids chemical synthesis, Sugar Acids chemical synthesis
Abstract

Eleven analogues of the C-terminal Ca(1)a(2)X motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC(50) = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.

Published
2004
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