Subramanyam J. Tantry

Practical and Efficient Synthesis of Orthogonally Protected α‐2,3‐Diaminopropionic Acid (2,3‐Dap), 2,4‐Diaminobutanoic Acid (2,4‐Dab), and their N‐Methylated Derivatives

Abstract The synthesis of orthogonally protected Fmoc‐Dap/Dab (Boc/Z/Alloc)‐OH starting from Fmoc‐Asp/Glu has been described. The salient features of our synthetic strategy involved formation of Fmoc‐Asp/Glu‐5‐oxazolidinone acids, conversion of acid function to acyl azides, Curtius rearrangement, and hydrolysis of the oxazolidinone group.

Microwave accelerated efficient synthesis of N-fluorenylmethoxycarbonyl/t-butoxycarbonyl/benzyloxycarbonyl-5-oxazolidinones

The synthesis of N-protected 5-oxazolidinones using amino acids, paraformaldehyde and p-toluene sulfonic acid in a minimum amount of toluene accelerated by microwave irradiation for 3 min in high yield is described.

Synthesis of peptides employing 9-fluorenylmethyl chloroformate as a coupling agent

The synthesis of peptides employing 9-fluorenylmethyl chloroformate(Fmoc-Cl) as a coupling agent has been described. The method is simple, efficient and rapid. All the peptides have been obtainedin good yield (70–95%). Furthermore, both the 1H NMR and the HPLC studies on Fmoc-Phg-Phe-OMe and Fmoc-D-Phg-Phe-OMe revealed that the coupling is free from racemization.

1-(t-Butyldimethylsilyloxy) benzotriazole (TBDMS-OBt): A new and novel reagent for the synthesis of peptides

Synthesis and use of 1-(t-butyldimethylsilyloxy)benzotriazole (TBDMS-OBt) in the coupling of Fmoc-amino acid chlorides to amino free amino acid esters in homogeneous solution phase is described. The coupling required no addition of base and was fast and racemization free. Work up and isolation of products were easy. Yield, purity and1H NMR analysis of peptides, synthesised by this method, were satisfactory.

Curtius Rearrangement Using Ultrasonication: Isolation of Isocyanates of Fmoc-Amino Acids and Their Utility for the Synthesis of Dipeptidyl Ureas

An efficient conversion of Nα-[(9–fluorenylmethyl)oxy]carbonyl (Fmoc) amino acid azides to the corresponding isocyanates using ultrasound is described. The Curtius rearrangement was accomplished using acid azides in toluene solution as well as solid powder at room temperature. All isocyanates synthesized have been obtained as crystalline solids and were characterized. Coupling of isocyanates with amino acid methyl ester hydrochloride salts in presence of N-methylmorpholine (NMM) resulted in Fmoc-protected dipeptidyl urea esters, which have been well characterized by 1H NMR, 13C NMR and mass spectrometry.

9-Fluorenylmethyl chloroformate (Fmoc-Cl) as a useful reagent for the synthesis of pentafluorophenyl, 2,4,5-trichlorophenyl, pentachlorophenyl, p-nitrophenyl, o-nitrophenyl and succinimidyl esters of N α -urethane protected amino acids

9-Fluorenylmethyl chloroformate has been demonstrated to be useful reagent for the synthesis of several commonly used active esters of Fmoc-/Boc-/Z-amino acids. These include pentafluorophenyl, 2,4,5-trichlorophenyl, pentachlorophenyl, p-nitrophenyl, o-nitrophenyl, and succinimidyl esters. The method is simple, rapid and efficient. All the compounds made have been isolated as crystaline solids in good yield and optical purity. They were fully characterized by IR, and 1H NMR.