Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids†

Characterization of SfmD as a Heme Peroxidase That Catalyzes the Regioselective Hydroxylation of 3-Methyltyrosine to 3-Hydroxy-5-methyltyrosine in Saframycin A Biosynthesis

“…Chemical Synthesis of Tyr Derivatives-The 3-methyl-Omethyltyrosine (3-Me-OMe-Tyr) and 3-OH-5-Me-OMe-Tyr were each prepared as described (6,14,15). Synthesis of 3-MeTyr and 3-hydroxy-5-methyltyrosine (3-OH-5-Me-Tyr) were achieved by following a previously reported method (6,14,15 supplemental Table S1.…”

“…Synthesis of 3-MeTyr and 3-hydroxy-5-methyltyrosine (3-OH-5-Me-Tyr) were achieved by following a previously reported method (6,14,15 supplemental Table S1. The purified PCR product was cloned into the EcoRI/HindIII site of pSP72 to generate pTL2039.…”

tert-Butyl (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionate

“…The title compound, (I), more simply known as N-Fmoc 3iodoalanine tert-butyl ester, is a useful starting material for the preparation of unnatural amino acids (Deboves et al, 2001), via its conversion to zinc and copper derivatives.…”

Synthesis of Halogenated α‐Amino Acids

“…Variously protected 3-iodoalanines are readily prepared from serine via displacement of a 3-tosylate with sodium iodide [18] and Jackson et al have utilized these products to good effect in organic synthesis via conversion of the iodide to an organozinc reagent ( [19] and references cited therein). For example, Fmoc-L-3-chloroalanine tert-butyl ester 17 was treated with sodium iodide in acetone to give protected 3-iodoalanine 18 in excellent yield (Scheme 10.6).…”