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Alpha-galactosyl ceramide new isomer and synthetic method thereof

A technology of galactosylceramide and synthesis method, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of high reactivity and instability of iodinated sugars, and achieves reduced operation difficulty and synthesis cost. Reduced, highly active effects

Active Publication Date: 2015-04-08
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Iodosugars were considered too reactive and unstable to be used in synthesis

Method used

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  • Alpha-galactosyl ceramide new isomer and synthetic method thereof
  • Alpha-galactosyl ceramide new isomer and synthetic method thereof
  • Alpha-galactosyl ceramide new isomer and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Construction of 4,5-cis sphingosine (see image 3 )

[0024] The raw material uses galactose with a relatively cheap structure as a chiral source. In the first step, acetal is formed to protect the 4 and 6 hydroxyl groups of galactose; in the second step, an aldehyde group is formed at the 3 hydroxyl, and the carbons at the 1 and 2 positions of the sugar are removed; in the third step, the Wittg reaction is used to react with Pre-synthesized tetradecylphosphorus ylide reaction to obtain 4,5-cis-alkene, which is a relatively critical step; the fourth step is to azidize the original 5-position hydroxyl on the carbon, and a carbon configuration occurs at this position Invert to obtain the desired configuration; the fifth step is deketalization reaction to obtain (2S,3R,4Z)-2-azido-1,3-diol derivatives.

[0025] The reported compounds were identified by mass spectrum or hydrogen spectrum; the new compounds were determined by nuclear magnetic resonance hydrogen spectrum, c...

Embodiment 2

[0039] Synthesis of new isomers of α-galactosylceramide (see Figure 4 )

[0040] First, sugar donors are synthesized, and full TMS galactose is synthesized from galactose. After simple treatment, TMS iodine sugar is obtained after reacting with iodine reagent. Without post-treatment, it immediately reacts with sugar acceptor-sphingosine under the action of a catalyst to obtain A single α-glycosyl isomer; then remove TMS on galactose under mild and simple conditions; the azide on the obtained compound is converted into an amino group, and because the compound is very active, it is directly put into the next step; the final amide reaction adopts The carboxylic acid is firstly derivatized into an active ester, and then reacted with an amino group to obtain a new isomer of α-galactosylceramide with mild conditions and a reasonable yield. The new compounds were determined by H-NMR and C-NMR spectra, and the final identification of the main compounds was by high-resolution mass sp...

Embodiment 3

[0054] (α-D-galactopyranose)-(1→1)-(2S,3R,4Z)-2-octadecylamido-4-octadecene-l,3-diol ( 1b )Synthesis

[0055] The synthesis method is the same as 1a , is just the compound 13b Alternative compound 13a , a white solid was obtained with a yield of 67%. 1 H NMR (400 MHz, MeOD: CDCl 3 = 1:3) δ 7.43 (1 H, s, CONH) 5.52 (1 H, dt, J =11.1, 7.5 Hz, H-5’), 5.33 (dd, 3 H, J =20.6, 8.1 Hz, H-4’, H- 9”, H-10”), 4.86 (1 H, d, J =3.5 Hz, H-1), 4.41 (d, 1 H, J =7.9 Hz, H-3'), 3.97-3.86 (m, 2 H, H-2', H-3), 3.79-3.66 (m, 7 H, H-1', H-2, H-4 , H-5, H-6), 2.15 (t, 2 H, J=7.5 Hz, H-6’), 2.00 (dd, 4 H, H-8”, H-11”), 1.56 (s, 1H, H-7’), 1.25 (m, 43 H, CH 2 ), 0.84 (t, 6 H, J =6.5 Hz, 2×CH 3 ). 13 C NMR (101 MHz, MeOD: CDCl 3 = 1:3) δ 174.47 (CONH), 133.70 (CH, CH=CH), 129.57 (CH, CH=CH), 129.31 (CH, CH=CH), 128.55 (CH, CH=CH), 99.67 (CH, americ C), 70.35 , 69.92, 69.40, 68.69, 67.25 (C-2, C-3, C-4, C-5, C-6), 66.99(C-3'), 61.42(C-1'), 53.66(CH, C-2'), 48.89(CH 2 , C-6...

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Abstract

The invention provides an alpha-galactosyl ceramide new isomer and its synthetic method. Configuration of sphingosine chain is changed to 4,5-cis double bond sphingosine chain. According to the invention, reaction steps are shortened, yield is raised, and aftertreatment and purification steps are omitted. The synthetic method can be used for total synthesis of similar glycosyl ceramide and satisfies wide range of development, research and application of different glycosyl ceramide.

Description

technical field [0001] The invention belongs to the field of total synthesis of glycolipid molecules, in particular to a new isomer of α-galactosylceramide and a synthesis method thereof. Background technique [0002] In the 90s of the 20th century, Kirin Breweries found that the extract of Agelas mauritianus sponge contained active molecules, and the structure of compound a was synthesized later. figure 1 (a-galactosylceramide, a-GalCer, KRN7000) has immune biological activity. α-Galactosylceramide (KRN 7000) is the most famous member of the glycosylceramide (glycosphingolipid) family, which is recognized by the antigen-presenting molecule CD1d to form a binary complex, and then binds to the NKT cell receptor (TCR ) interaction, activate the signal transmission molecules responsible for intercellular communication, namely cytokines, and the cytokine Th1 / Th2 immune response activates specific other immune cells (B cells, T cells, macrophages, etc.) to play anti-tumor and a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/10C07H1/00
CPCC07H1/00C07H15/10
Inventor 崔艳丽程照东张勇民毛建卫
Owner ZHEJIANG UNIV
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