1622984-07-9

Upstream product

• 35661-60-0 Fmoc-Leu-OH 
• 35661-40-6 N-Fmoc L-Phe 
• 71989-26-9 Fmoc-Lys(tert-butoxycarbonyl) 
• 144120-54-7 Nα-(9-fluorenylmethoxycarbonyl)-L-glutamic acid α-allyl ester 
• 142-62-1 hexanoic acid 
• 204777-78-6 Fmoc-Lys(ivDde)-OH 
• 174653-61-3 N_α-(9-fluorenylmethoxycarbonyl)-N_ε-(2-nitrobenzyloxycarbonyl)-lysine 
• 471-25-0 Propiolic acid 

Relevant academic research and scientific papers

Solid-phase synthesis of cyclic lipopeptidotriazoles

The solid-phase synthesis of cyclic lipopeptidotriazoles derived from the cyclic decapeptide c(Lys-Lys2-Leu-Lys-Lys5-Phe-Lys-Lys- Leu-Gln) (BPC194), incorporating a triazolyl ring at Lys2 and a hexanoyl group at Lys5, was studied. Four different strategies that required the use of five orthogonal protecting groups (Fmoc, tBu, All, pNZ, ivDde) were explored. The influence of the side-chain protection of Lys 2 and Lys5 with the ivDde and pNZ groups was evaluated by incorporating Lys2(ivDde)/Lys5(pNZ) or Lys 2(pNZ)/Lys5(ivDde). The order of removal of these protecting groups and of the introduction of the hexanoyl and triazolyl moieties was also studied. The best strategy included: (i) synthesis of a cyclic peptidyl resin bearing Lys2(ivDde) and Lys5(pNZ); (ii) pNZ group removal; (iii) acylation with hexanoic acid; (iv) ivDde group removal; and (v) acylation with propiolic acid followed by an azide-alkyne 1,3-dipolar cycloaddition. By using this protocol, a set of cyclic lipopeptidotriazoles was prepared in high purities.