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Preparation of N ‐Fmoc‐Protected ( S )‐5‐Amino‐4,4‐difluoro‐7‐methyloctanoic Acid, a Possible Dipeptide Isostere
Author(s) -
Deniau Gildas,
Seebach Dieter
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900215
Subject(s) - isostere , chemistry , dipeptide , stereochemistry , peptide , amino acid , proteases , peptidomimetic , protecting group , combinatorial chemistry , organic chemistry , biochemistry , enzyme , alkyl
The title compound 1 was prepared from L ‐leucine. The key steps include a Grignard addition to Bn 2 ‐leucinal, a CO/CF 2 replacement with Et 2 NSF 3 (DAST) and use of a Ph group as synthetic equivalent of a COOH group. The difluoro‐ δ ‐amino acid 1 was incorporated into a peptide 8 ; tests with various proteases showed no inhibition by this particular peptide.