Protection of the hydroxyl function of hydroxyproline and serine in peptide synthesis by the 2‐methoxyethoxymethyl (Mem) group

Vadolas, D.; Germann, H.‐P.; Thakur, Suman; Keller, W.; Heidemann, E.

doi:10.1111/j.1399-3011.1985.tb02210.x

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1986

2019

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Cited by 11 publications

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“…Cleavage with TFA in dichloromethane was sluggish; treatment with TiCl 4 sometimes gave good results, but was not reproducible. Ultimately, treatment with hydrochloric acid in TFA was the most effective and reliable. Protection of the four alcohols as TBS ethers was uneventful.…”

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confidence: 99%

Total Synthesis of Alloviroidin

2019

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Alloviroidin is a cyclic heptapeptide, produced by several species of Amanita mushrooms, that demonstrates high affinity for F-actin as is characteristic of virotoxins and phallotoxins. Alloviroidin was synthesized via a [3 + 4] fragment condensation of Fmoc-d-Thr(OTBS)-d-Ser(OTBS)-(2S,3R,4R)-DHPro(OTBS)2-OH and H-Ala-Trp(2-SO2Me)-(2S,4S)-DHLeu(5-OTBS)-Val-OMe to form bond A. The linear heptapeptide favored a turn conformation, facilitating cyclization between Val1 and d-Thr2 (position B). Global deprotection and HPLC purification afforded alloviroidin with NMR spectra in excellent agreement with the natural product.

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confidence: 99%