1998
DOI: 10.1016/s0008-6215(98)00082-2
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Synthesis of a neoglycoprotein containing the Lewis X analogous trisaccharide β-d-GalpNAc-(1→4)[α-l-Fucp-(1→3)]-β-d-GlcpNAc

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Cited by 37 publications
(20 citation statements)
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“…The accepted pathway for the biosynthesis of the sLe x and sLe a structures starts by sialylation of the type-2 and type-1 chain precursors, respectively, followed by fucosylation of the sialylated intermediates. [17][18][19][20][21] In embryogenesis, sialylation is an early phenomenon that appears at the beginning of cell differentiation and precedes fucosylation. 22 The step of fucosylation is then rate-limiting for the formation of sLe x/a in many different cell types and tissues.…”
Section: Discussionmentioning
confidence: 99%
See 1 more Smart Citation
“…The accepted pathway for the biosynthesis of the sLe x and sLe a structures starts by sialylation of the type-2 and type-1 chain precursors, respectively, followed by fucosylation of the sialylated intermediates. [17][18][19][20][21] In embryogenesis, sialylation is an early phenomenon that appears at the beginning of cell differentiation and precedes fucosylation. 22 The step of fucosylation is then rate-limiting for the formation of sLe x/a in many different cell types and tissues.…”
Section: Discussionmentioning
confidence: 99%
“…The mixture was incubated for 16 hours at 37°C and the reaction was stopped by the addition of 3 ml of cold water and centrifuged. The supernatant was added to the Sep-Pak C 18 cartridge, the unreacted GDP-[ 14 C ]-fucose and its hydrolysis products were washed out with 25 ml of H 2 O. Radiolabeled reaction products were eluted with methanol and counted in a liquid scintillation counter.…”
Section: Measurement Of Fucosyltransferase Activitymentioning
confidence: 99%
“…However, since fucosyl residues at O-3 of glucosamine units are known 16 to be unstable when treated in acidic conditions, this reduction was left to proceed at room temperature rather than heated to 50 or 60 o C. After 7 h of reaction at this temperature, TLC showed complete disappearance of the starting material and formation of one major and one minor product. The major product was identified as chloroacetamide 33 (79%), and the minor product was characterized as the fully reduced acetamide 34 isolated in 11% yield.…”
Section: Introductionmentioning
confidence: 99%
“…The synthesis of some only slightly modified Le" analogs containing Glc instead of GlcNAc [78], GalNAc instead of Gal [79], or 5-thiofucose instead of Fuc [ 801 has been similarly performed as described above using trichloroacetimidate donors. It has been found that sialylations are always crucial and expensive processes, therefore many syntheses for sLeX mimetics have been developed in which neuraminic acid is replaced by other acids (Scheme 18).…”
Section: Ga@( 1 -4)glcnacp-x Neuaca(2-3) Fuca(1-3)mentioning
confidence: 99%