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Synthesis of Hydroxylated Analogues of α‐Galactosyl Ceramide (KRN7000) with Varying Stereochemistry
Author(s) -
Sawant Ratnnadeep C.,
Hung JungTung,
Chuang HueiLin,
Lin HuanShuan,
Chen WanShin,
Yu Alice L.,
Luo ShunYuan
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301111
Subject(s) - chemistry , ceramide , stereochemistry , sphingosine , galactose , sphingolipid , mannose , biochemistry , apoptosis , receptor
The synthesis of analogues of α‐galactosyl ceramide (KRN7000) with an additional hydroxy group in the phytosphingosine chains and with varying stereochemistry is described. Careful selection of glucose, galactose, mannose, and talose hexopyranoses allowed us to control the stereochemistry of some of the hydroxy groups in the sphingosine chain to give some interesting hydroxylated KRN7000 analogues.