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Synthesis of hydroxyethylene and ketomethylene dipeptide isosteres

✍ Scribed by Mark W. Holladay; Daniel H. Rich

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
210 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

A general stereo-directed synthesis of "ketomethylene" and "hydroxyethylene" dipeptide isosteres is reported. Peptides containing the amino acids, (2&%)-5-amino-4-oxo-2,8dimethyloctanoic acid (the "ketomethylene" analog of L-Leu-L-Ala), and (2&,5z)-5-amino-4-hydroxy-2,8-dimethyloctanoic acid (the "hydroxyethylene" analog of L-Leu-L-Ala) were synthesized as analogs of pepstatin with statine replaced by the Leu-Ala isosteres. Dipeptide isosteres, i.e. dipeptides in which the amide -CONH-linkage has been replaced by some approximately isosteric functional group, eg. the ketomethylene,Ip2 hydroxyethylene,2 thioamide,3 C-C double bond4 or thiomethylene group,5 have been used to prepare either metabolically stable peptides or mechanism based enzyme inhibitors.

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