Preparation of  N ‐Fmoc‐Protected ( S )‐5‐Amino‐4,4‐difluoro‐7‐methyloctanoic Acid, a Possible Dipeptide Isostere | Zendy

Deniau Gildas | Zendy; Seebach Dieter | Zendy

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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.

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