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Fmoc-D-Arg(Pbf)-OH [187618-60-6]


Other Names: Nα-Fmoc-Ng-Pbf-D-arginine;Nα-(9-fluorenylmethoxycarbonyl)-Ng-(2,2,4,6,7-pentamethyldihydrobenzfuran-5-sulfonyl)-D-arginine

Catalog #: AFR205

CAS 187618-60-6

Formula C34H40N4O7S

Molecular Weight 648.8




Fmoc-D-Arg(Pbf)-OH is the commonly utilized D-arginine derivative in solid phase peptide synthesis.  It has been applied to the preparation of antimicrobial peptide analogs.  One possible application of Fmoc-D-Arg(Pbf) is in the antimicrobial peptide RLA.  Substituting  D-arginine for D-lysine improved membrane permeability and increased mitochondrial accumulation (I. Nakase, et al., Chem. Commun. (Camb.), 2012, 48, 11097-9).  A cyclic dipeptide containing D-arginine, from Bacillus cereus, has antifungal activity and also shows significant activity against breast cancer (S.K. Nishanth, B. Namisan, C. Dileep, Peptides, 2014, 53, 59-69).  Fmoc-D-Arg(Pbf)-OH is also useful in preparing analogs of the antimicrobial peptide oncocin.  Replacing the two L-Arg residues oncocin with D-Arg increased the bioavailability from 25 minutes to over 8 hours while also slightly improving the antibacterial activity (D. Knappe, N. Kabankov, R. Hoffmann, Int. J. Antimicrob. Agents, 2011, 37, 166-70).

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AZR202 Z-D-Arg-OH HCl AZR210 Z-D-Arg(Mtr)-OH CHA
AZR205 Z-D-Arg(Pbf)-OH