Practical syntheses of optically active carbagalactose and their potential application to the carbocyclic analogues of KRN7000

Yu, Seok‐Ho; Park, Jeong-Ju; Chung, Sung‐Kee

doi:10.1016/j.tetasy.2006.11.014

Cited by 11 publications

(5 citation statements)

References 35 publications

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“…100 Several diastereoisomers were also obtained by Franck's team during their studies on the use of SAE reactions to prepare C-glycosyl derivatives (see Scheme 4D). 98 The diastereoisomers (2¢S, 3¢S, 4¢S) (113), (2¢R, 3¢S, 4¢R) (114) and (2¢R, 3¢S, 4¢S) (115) were separated and tested (Table 5). These unnatural compounds were less active than KRN 7000 and the results close to those observed for the O-GalCer stereoisomers (see Table 3).…”

Section: A) Modification Of the Backbone Structure Kirinmentioning

confidence: 99%

“…This section describes the various other KRN 7000-based analogues synthesized in the literature. Following works initiated by Chung and co-workers in 2006, 115 Mori's team achieved the syn-thesis of a carbocyclic analogue RCAI-56 (7) in order to evaluate the impact of the intracyclic oxygen in the sugar and to replace the glycoside linkage with a stronger ether bond (Fig. 14).…”

Section: Other Analogues: Carbaglycosides Inositol- Myoinositol- Seri...mentioning

confidence: 99%

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The stimulating adventure of KRN 7000

et al. 2011

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Associated with the CD1d protein, KRN 7000, a potent synthetic α-galactosylceramide, is known to activate the invariant NKT immune cells. This stimulation then leads to the production of different cytokines modulating a T(H)1/T(H)2 immune response balance involved in protection against several pathologies such as autoimmune diseases and cancers. Various efforts have been made toward the synthesis of simple and more functionalized analogues in order to selectively induce T(H)1 or T(H)2-type cytokine production. Since the discovery of KRN 7000, structure-activity relationships, crystallographic and modelling studies have pointed to the potential of several GalCer analogues in term of selective bioactivity, and have highlighted interesting elements in order to better understand the recognition and activation mechanisms of immune iNKT cells. By presenting an up-to-date library of analogues, collecting recent breakthroughs done in crystallography and molecular modelling, and relating them to the available biological results, we hope that this review will highlight and help the scientific community in their KRN research.

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Section: A) Modification Of the Backbone Structure Kirinmentioning

confidence: 99%

Section: Other Analogues: Carbaglycosides Inositol- Myoinositol- Seri...mentioning

confidence: 99%

The stimulating adventure of KRN 7000

et al. 2011

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“…Other synthetic alterations have been used to create α-carba-GalCer analogs [51] . In 2009, carbasugar and cyclitol analogs of αGalCer were generated, and another three analogs, RCAI-56 (a carba-α- d -galactose analog), RCAI-59 (a 1-deoxy-neo-inositol analog), and RCAI-92 (a 1-O-methylated analog), also were found to be Th1 skewing lipids [52] .…”

Section: Introductionmentioning

confidence: 99%

Antigen specificity of invariant natural killer T-cells

Birkholz

Kronenberg

2015

Biomedical Journal

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Natural killer T-cells, with an invariant T-cell antigen receptor α-chain (iNKT cells), are unique and conserved subset of lymphocytes capable of altering the immune system through their rapid and potent cytokine responses. They are reactive to lipid antigens presented by the CD1d molecule, an antigen-presenting molecule that is not highly polymorphic. iNKT cell responses frequently involve mixtures of cytokines that work against each other, and therefore attempts are underway to develop synthetic antigens that elicit only strong interferon-gamma (IFNγ) or only strong interleukin-4 responses but not both. Strong IFNγ responses may correlate with tighter binding to CD1d and prolonged stimulation of iNKT cells, and this may be useful for vaccine adjuvants and for stimulating anti-tumor responses. iNKT cells are self-reactive although the structure of the endogenous antigen is controversial. By contrast, bacterial and fungal lipids that engage the T-cell receptor and activate IFNγ from iNKT cells have been identified from both pathogenic and commensal organisms and the responses are in some cases highly protective from pathogens in mice. It is possible that the expanding knowledge of iNKT cell antigens and iNKT cell activation will provide the basis for therapies for patients suffering from infectious and immune diseases and cancer.

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“…IR spectrum (CCl 4 ), ν, cm -1 : 3640, 3541. 1 [66]. A solution of 1.133 g (6.51 mmol) of alcohol 11 in 60 mL of anhydrous THF was cooled to 0°C, and 0.52 g (13 mmol) of sodium hydride (60% suspension in mineral oil) was added in portions under argon.…”

Section: -[(4s5s)-225-trimethyl-13-dioxan-4-yl]ethanol (11)mentioning

confidence: 99%

New synthesis of syn-stereodiad building block for polyketides. Formal synthesis of arenamides A and C

Shklyaruck

2015

Russ J Org Chem

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An efficient procedure has been developed for the transformation of (7S)-7-(3-bromoprop-1-en-2yl)-5,5-dimethyl-4,6-dioxaspiro[2.5]octane [available from diethyl (S)-malate] into methyl 2-[(4S)-2,2-dimethyl-5-methylidene-1,3-dioxan-4-yl]acetate, and conditions for diastereoselective reduction of the double C=C bond in the latter have been optimized. The reduction product has been converted into (3S,4S)-3-[tertbutyl(dimethyl)siloxy]-4-methyldecanoic acid which is a building block for the synthesis of arenamides A and C, natural compounds possessing pronounced antitumor activity and efficiently inhibiting nitrogen(II) oxide and prostaglandin E 2 (PGE 2 ). * Stereodiad (propionate) block is a three-carbon fragment with vicinal hydroxy and methyl substituents in polyketide molecules.

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Practical syntheses of optically active carbagalactose and their potential application to the carbocyclic analogues of KRN7000

Cited by 11 publications

References 35 publications

The stimulating adventure of KRN 7000

The stimulating adventure of KRN 7000

Antigen specificity of invariant natural killer T-cells

New synthesis of syn-stereodiad building block for polyketides. Formal synthesis of arenamides A and C

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