Studies on the Thioglycosides ofN-Acetylneuraminic Acid. 6: Synthesis of Ganglioside GM4Analogs1

Ito, Yukiteru; Kiso, Makoto; Hasegawa, Akira

doi:10.1080/07328308908048010

Cited by 87 publications

(11 citation statements)

References 8 publications

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“…Consequently, we adopted the azido-sphingosine acceptor as the ceramide precursor because it provides a better yield on coupling than when a ceramide acceptor is used, although the resulting azidosphingosine requires further transformation to ceramide. In our laboratory, 3-O-Bz-protected [25] or 3-O-TBDPSprotected [26] azido-sphingosine acceptor has been frequently used for gangliosides syntheses; however, we adopted the 3-O-PMB-protected azido-sphingosine acceptor 22 [27]; this acceptor is prepared from the unprotected azido-sphingosine [28,29] in three steps and is more reactive due to the nucleophilicity of the acceptor alcohol, which is enhanced by the electron-donating PMB group. The use of this acceptor led to the formation of β-glycosyl lipid.…”

Section: Resultsmentioning

confidence: 99%

Design and efficient synthesis of novel GM2 analogues with respect to the elucidation of the function of GM2 activator

et al. 2008

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To elucidate the mechanism underlying the hydrolysis of the GalNAcbeta1-->4Gal linkage in ganglioside GM2 [GalNAcbeta1-->4(NeuAcalpha2-->3)Galbeta1-->4Glcbeta1-->1' Cer] by beta-hexosaminidase A (Hex A) with GM2 activator protein, we designed and synthesized two kinds of GM2 linkage analogues-6'-NeuAc-GM2 and alpha-GalNAc-GM2. In this paper, the efficient and systematic synthesis of these GM2 analogues was described. The highlight of our synthesis process is that the key intermediates, newly developed sialyllactose derivatives, were efficiently prepared in sufficient quantities; these derivatives directly served as highly reactive glycosyl acceptors and coupled with GalNTroc donors to furnish the assembly of GM2 tetrasaccharides in large quantities.

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Section: Resultsmentioning

confidence: 99%

Design and efficient synthesis of novel GM2 analogues with respect to the elucidation of the function of GM2 activator

et al. 2008

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“…For the synthesis of 12, a nine step procedure was chosen [31,32]. We have previously reported on the preparation of 3d-deoxy Le x pentasaccharide 8 [29] and 4d-deoxy Le x pentasaccharide 9 [30] through a convergent synthetic route, using the building block 4-7, as shown in Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

First synthesis of two deoxy Lewisx pentaosyl glycosphingolipids

et al. 2007

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The Lewis(x)-Lewis(x) interaction has been increasingly studied, using a variety of techniques including nuclear magnetic resonance spectroscopy, mass spectrometry, vesicle adhesion, atomic force microscopy, and surface plasmon resonance spectroscopy. However, the detailed molecular mechanism of these weak, divalent cation dependent interactions remains unclear, and new models are needed to probe the nature of this phenomenon in term of key roles of the different hydroxyl groups on Lewis(x) trisaccharide determinant involved in the Lewis(x)-Lewis(x) interaction. An interesting solution is to synthesize a series of Lewis(x) pentaosyl glycosphingolipid derivatives in which one of the eight hydroxyl groups of Lewis(x) trisaccharide is replaced by a hydrogen atom, and to test the adhesion induced by interaction of these derivatives, in order to gain insight into the functions played by the hydroxyl groups of the Lewis(x) trisaccharide. This article describes the synthesis of 3d-deoxy and 4d-deoxy Lewis(x) pentaosyl glycosphingolipids, to be used for study of the Lewis(x)-Lewis(x) interaction.

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“…Development of glycoconjugate analogues that are metabolically stable has also been an active area of research. In the case of ganglioside analogues, sialidase would first cleave the glycosidic linkage of sialic acid (O‐sialoside) [22]. Therefore, the development of sialidase‐resistant analogues was investigated, and S‐linked GM4 ( 19 ), in which the oxygen atom of the O‐sialoside bond was replaced by a sulfur atom, was developed by Hasegawa in 1989 [23].…”

Section: Mimicking the Glycosidic Linkage Of Sialic Acid: A Sialidasementioning

confidence: 99%

Mimicking/Extracting Structure and Functions of Natural Products: Synthetic Approaches that Address Unexplored Needs in Chemical Biology

Hirai

2014

The Chemical Record

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Natural products are often attractive and challenging targets for synthetic chemists, and many have interesting biological activities. However, synthetic chemists need to be more than simply suppliers of compounds to biologists. Therefore, we have been seeking ways to actively apply organic synthetic methods to chemical biology studies of natural products and their activities. In this personal review, I would like to introduce our work on the development of new biologically active compounds inspired by, or extracted from, the structures of natural products, focusing on enhancement of functional activity and specificity and overcoming various drawbacks of the parent natural products.

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Studies on the Thioglycosides ofN-Acetylneuraminic Acid. 6: Synthesis of Ganglioside GM₄Analogs¹

Cited by 87 publications

References 8 publications

Design and efficient synthesis of novel GM2 analogues with respect to the elucidation of the function of GM2 activator

Design and efficient synthesis of novel GM2 analogues with respect to the elucidation of the function of GM2 activator

First synthesis of two deoxy Lewisx pentaosyl glycosphingolipids

Mimicking/Extracting Structure and Functions of Natural Products: Synthetic Approaches that Address Unexplored Needs in Chemical Biology

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