A practical and enantioselective synthesis of glycosphingolipids and related compounds.  Total synthesis of globotriaosylceramide (Gb3)

Nicolaou, K. C.; Caulfield, Thomas J.; Kataoka, Hiromi; Kumazawa, Toshiaki

doi:10.1021/ja00231a071

Cited by 126 publications

(41 citation statements)

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“…The sphingosine progenitor was synthesized according to the method of Schmidt and Zimmermann. 7 The coupling of sphingosine with a trisaccharide fragment was carried out as reported by Nicolaou et al, 8 with minor modifications.…”

Section: Synthesis Of Lyso Gb3mentioning

confidence: 99%

Effect of a soluble pseudo-receptor on verotoxin 2-induced toxicity

Takenaga

Igarashi

Higaki

et al. 2000

Journal of Infection and Chemotherapy

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Section: Synthesis Of Lyso Gb3mentioning

confidence: 99%

Effect of a soluble pseudo-receptor on verotoxin 2-induced toxicity

Takenaga

Igarashi

Higaki

et al. 2000

Journal of Infection and Chemotherapy

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“…The azide function in the protected glycolipids 23 and 24 was reduced to that of an amine by triphenylphosphine dissolved in a small amount of water, in benzene at 50°C [30]; subsequent condensation with stearic acid by EDC and DMAP in 1,2-dichloroethane at 40°C afforded the protected GM2 analogues 26 and 29 in 88% and 79% yield (two steps), respectively. The cleavage of the PMB group proceeded smoothly due to the use of TFA in CH 2 Cl 2 .…”

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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“…This twostep activation sequence can be reiterated; for this purpose the leaving group of the obtained disaccharide LG a is again converted into LG b and so on. This concept was discovered for S-ethyl (LG a ) and bromo (LG b ) moieties [173] and further explored for other systems [176,[192][193][194]. The same principle was applied by Danishefsky in the reiterative glycal assembly approach [43,195,196].…”

Section: Two-step Activation and Preactivation Strategiesmentioning

confidence: 94%