Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

Jeong Ju Park; Ji Hyung Lee; Subhash C. Ghosh; Gabriel Bricard; Manjunatha M. Venkataswamy; Steven A. Porcelli; Sung Kee Chung

doi:10.1016/j.bmcl.2008.06.036

Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

Jeong Ju Park
, Ji Hyung Lee
, Subhash C. Ghosh
, Gabriel Bricard
, Manjunatha M. Venkataswamy
, Steven A. Porcelli
, Sung Kee Chung

Microbiology & Immunology

Research output: Contribution to journal › Article › peer-review

40 Scopus citations

Abstract

KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined. Crown

Original language	English (US)
Pages (from-to)	3906-3909
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	14
DOIs	https://doi.org/10.1016/j.bmcl.2008.06.036
State	Published - Jul 15 2008

Keywords

KRN7000 stereoisomers
NKT cell
Phytosphingosine
α-GalCer

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2008.06.036

Cite this

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title = "Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand",

abstract = "KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined. Crown",

keywords = "KRN7000 stereoisomers, NKT cell, Phytosphingosine, α-GalCer",

author = "Park, \{Jeong Ju\} and Lee, \{Ji Hyung\} and Ghosh, \{Subhash C.\} and Gabriel Bricard and Venkataswamy, \{Manjunatha M.\} and Porcelli, \{Steven A.\} and Chung, \{Sung Kee\}",

note = "Funding Information: This work was supported by the Korea Research Foundation grant funded from the Korean Government (MOEHRD: KRF-2005-070-C00078).",

year = "2008",

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day = "15",

doi = "10.1016/j.bmcl.2008.06.036",

language = "English (US)",

volume = "18",

pages = "3906--3909",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

AU - Park, Jeong Ju

AU - Lee, Ji Hyung

AU - Ghosh, Subhash C.

AU - Bricard, Gabriel

AU - Venkataswamy, Manjunatha M.

AU - Porcelli, Steven A.

AU - Chung, Sung Kee

N1 - Funding Information: This work was supported by the Korea Research Foundation grant funded from the Korean Government (MOEHRD: KRF-2005-070-C00078).

PY - 2008/7/15

Y1 - 2008/7/15

N2 - KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined. Crown

AB - KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined. Crown

KW - KRN7000 stereoisomers

KW - NKT cell

KW - Phytosphingosine

KW - α-GalCer

UR - https://www.scopus.com/pages/publications/47149113110

UR - https://www.scopus.com/pages/publications/47149113110#tab=citedBy

U2 - 10.1016/j.bmcl.2008.06.036

DO - 10.1016/j.bmcl.2008.06.036

M3 - Article

C2 - 18586489

AN - SCOPUS:47149113110

SN - 0960-894X

VL - 18

SP - 3906

EP - 3909

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 14

ER -

Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

Abstract

Keywords

ASJC Scopus subject areas

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