Total Solid-Phase Synthesis of Dehydroxy Fengycin Derivatives
A rapid and efficient solid-phase strategy for the synthesis of dehydroxy fengycins derivatives is described. This synthetic approach involved the linkage of a Tyr to a Wang resin via a Mitsunobu reaction and the elongation of the peptide sequence followed by subsequent acylation of the N-terminus of the resulting linear peptidyl resin, esterification of the phenol group of a Tyr with an Ile, and final macrolactamization. The amino acid composition as well as the presence of the N-terminal acyl group significantly influenced the stability of the macrolactone. Cyclic lipodepsipeptides with a l-Tyr3/d-Tyr9 configuration were more stable than those containing the Tyr residues with an opposite configuration. This work constitutes the first approach on the total solid-phase synthesis of dehydroxy fengycin derivatives.
Rosés, Cristina,Camó, Cristina,Oliveras, àngel,Moll, Lluis,López, Nerea,Feliu, Lidia,Planas, Marta
p. 15297 - 15311
(2019/01/04)
p-Nitrobenzyloxycarbonyl (pNZ) as a temporary Na-protecting group in orthogonal solid-phase peptide synthesis - Avoiding diketopiperazine and aspartimide formation
p-Nitrobenzyloxycarbonyl (pNZ) was used as a temporary protecting group for α-amino functionalities in solid-phase peptide synthesis. The corresponding derivatives are readily synthesized solids that perform well on solid phase. The pNZ moiety is orthogonal with the most common protecting groups used in peptide chemistry, and is removed under neutral conditions in the presence of catalytic amounts of acid. The use of pNZ derivatives in conjunction with Fmoc chemistry circumvents typical side reactions associated with the use of piperidine, such as DKP and aspartimide formation. The flexibility of pNZ can be exploited for the preparation of libraries of small organic molecules. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Isidro-Llobet, Albert,Guasch-Camell, Judit,Alvarez, Mercedes,Albericio, Fernando
p. 3031 - 3039
(2007/10/03)
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