Open AccessChemical Synthesis of Human Milk Oligosaccharides: Lacto-N-hexaose Galβ1→3GlcNAcβ1→3 [Galβ1→4GlcNAcβ1→6] Galβ1→4Glc
Author(s) -
Mithila D. Bandara,
Keith J. Stine,
Alexei V. Demchenko
Publication year - 2019
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.9b02701
Subject(s) - chemistry , oligosaccharide , glycosylation , protecting group , stereochemistry , chemical synthesis , acceptor , combinatorial chemistry , biochemistry , organic chemistry , in vitro , alkyl , physics , condensed matter physics
The first synthesis of lacto- N -hexaose (LNH) has been completed using a convergent strategy. The donor-acceptor protecting-leaving group combinations were found to be of paramount significance for achieving successful glycosylations and minimizing side reactions. Lacto- N -tetraose, another common human milk oligosaccharide, was also obtained en route to the target LNH.