Fmoc-3-[[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-L-alanine

N-alpha-Fmoc-N-beta-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,3-diaminopropionic Acid is used in the synthesis of phenylpyrazolo[3,4-d]pyrimidine-peptide conjugates as Src kinase inhibitors. It is also used to prepare peptidomimetic ligands for α4β1 integrin on Jurkat T-leukemia cells.

This orthogonally-protected diaminopropionic acid derivative is based on the hindered Dde variant ivDde. The side-chain ivDde group is considerably more stable to piperidine than Dde and is less prone to migrate from protected to unprotected side-chains [1]. However, migration from side-chain to the unprotected α-amino group of Dpr is unavoidable [2]. This side-reaction can, however, be minimized by the appropriate choice of coupling method for the subsequent residue, see [3].

When removing ivDde in the presence of allyl-based protecting groups, allyl alcohol should be included in the deprotection solution to prevent reduction of the allyl group [4].

The product number for this product was previously 04-12-1195.

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reaction type: Fmoc solid-phase peptide synthesis