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Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry.

ABSTRACT: KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release a broad range of bioactive cytokines. In an effort to understand the structure-activity relationships, we have carried out syntheses of 26 new KRN7000 analogues incorporating aromatic residues in either or both side chains. Structural variations of the phytosphingosine moiety also include varying stereochemistry at C3 and C4, and 4-deoxy and 3,4-dideoxy versions. Their biological activities are described.

SUBMITTER: Park JJ

PROVIDER: S-EPMC5584937 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry.

Park Jeong-Ju JJ Lee Ji Hyung JH Seo Kyung-Chang KC Bricard Gabriel G Venkataswamy Manjunatha M MM Porcelli Steven A SA Chung Sung-Kee SK

Bioorganic & medicinal chemistry letters 20100104 3

KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release a broad range of bioactive cytokines. In an effort to understand the structure-activity relationships, we have carried out syntheses of 26 new KRN7000 analogues incorporating aromatic residues in either or both side chains. Structural variations of the phytosphingosine moiety also include varying stereochemistry at C3 and C4, and 4-deoxy and 3,4-dideoxy versions. Their b ...[more]

PMID: 20061147

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