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Facile Synthesis of a β(1‐3)‐Linked gal‐galactal Disaccharide and Its Use in N ‐Iodosuccinimide‐Activated O ‐Glycopeptide Synthesis
Author(s) -
Kessler Horst,
Kling Andreas,
Kottenhahn Matthias
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199004251
Subject(s) - glycopeptide , disaccharide , glycophorin , derivative (finance) , chemistry , yield (engineering) , combinatorial chemistry , protein subunit , stereochemistry , biochemistry , materials science , membrane , gene , metallurgy , antibiotics , financial economics , economics
The fact that compound 1 can now be synthesized in four steps with an overall yield of 21 % should ensure its broader utilization in the NIS‐activated synthesis of glycopeptides. The key intermediate in the process is the selectively protected galactaldehyde derivative 2.1 reacts not only with the universally applicable Fmoc‐Ser‐OBzl subunit but also with a cyclic glycophorin‐A fragment.