Total synthesis of novel subclass of glyco-amino acid structure motif: C2-α-L-C-mannosylpyranosyl-L-tryptophan [17]

Journal of the American Chemical Society

Volumn 121, Issue 41, 1999, Pages 9754-9755

  Manabe, Shino ^a   Ito, Yukishige ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; C2 ALPHA LEVO MANNOSYLPYRANOSYL TRYPTOPHAN; EPOXIDE; GLYCOPROTEIN; INDOLE DERIVATIVE; MANNOSE; RIBONUCLEASE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO ACID SYNTHESIS; LETTER; PROTEIN CONFORMATION; PROTEIN GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032749163     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990926a     Document Type: Letter

References (30)

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30. Further incorporation of a Phe residue was successfully performed to give hexapeptide corresponding to 1 in a fully protected form. However, the final deprotection turned out to be problematic, presumably due to the instability of mannosylated tryptophan portion under acidic conditions required for the complete removal of t-Bu and Boc groups. This problem would be solved by making slight modification of amino acid protection strategy (Fmoc/ benzyl), which is currently under investigation.