Synthesis of chimera oligopeptide including furanoid ß-sugar amino acid derivatives with free OHs: mild but successful removal of the 1,2-O-isopropylidene from the building block.
Amino Acids
; 53(2): 281-294, 2021 Feb.
Article
em En
| MEDLINE
| ID: mdl-33559000
ABSTRACT
Complementary to hydrophobic five membered ring ß-amino acids (e.g. ACPC), ß-sugar amino acids (ß-SAAs) have found increasing application as hydrophilic building blocks of foldamers and α/ß chimeric peptides. Fmoc-protected ß-SAAs [e.g. Fmoc-RibAFU(ip)-OH] are indeed useful Lego elements, ready to use for SPPS. The removal of 1,2-OH isopropylidene protecting group increasing the hydrophilicity of such SAA is presented here. We first used N3-RibAFU(ip)-OH model compound to optimize mild deprotection conditions. The formation of the 1,2-OH free product N3-RibAFU-OH and its methyl glycoside methyl ester, N3-RibAFU(Me)-OMe were monitored by RP-HPLC and found that either 50% TFA or 8 eqv. Amberlite IR-120 H+ resin in MeOH are optimal reagents for the effective deprotection. These conditions were then successfully applied for the synthesis of chimeric oligopeptide -GG-X-GG- [X=RibAFU(ip)]. We found the established conditions to be effective and-at the same time-sufficiently mild to remove 1,2-O-isopropylidene protection and thus, it is proposed to be used in the synthesis of oligo- and polypeptides of complex sequence combination.
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01-internacional
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MEDLINE
Assunto principal:
Oligopeptídeos
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Alcenos
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Açúcares
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Aminoácidos
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article