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[ CAS No. 15839-70-0 ] {[proInfo.proName]}

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Chemical Structure| 15839-70-0
Chemical Structure| 15839-70-0
Structure of 15839-70-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 15839-70-0 ]

CAS No. :15839-70-0 MDL No. :MFCD00870977
Formula : C16H25N5O15P2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 589.34 Pubchem ID :-
Synonyms :
GDP-L-fucose
Chemical Name :(((2R,3S,4R,5R)-5-(2-Amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl) methyl) ((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl) dihydrogen diphosphate

Safety of [ 15839-70-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15839-70-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 15839-70-0 ]

[ 15839-70-0 ] Synthesis Path-Downstream   1~88

  • 1
  • guanosine 5'-diphospho-D-mannose [ No CAS ]
  • [ 15839-70-0 ]
  • 2
  • [ 7390-53-6 ]
  • [ 16562-58-6 ]
  • [ 15839-70-0 ]
  • 3
  • β-L-Fucopyranosyl phosphate bis(tri-n-octylammonium) salt [ No CAS ]
  • Guanosine 5'-phosphoromorpholidate N,N'-dicyclohexyl-4-morpholine carboxamidinium salt [ No CAS ]
  • [ 15839-70-0 ]
  • 4
  • [ 86733-47-3 ]
  • [ 15839-70-0 ]
  • [ 141612-83-1 ]
  • 5
  • [ 143398-10-1 ]
  • [ 15839-70-0 ]
  • [ 143398-11-2 ]
  • 6
  • [ 142810-05-7 ]
  • [ 15839-70-0 ]
  • [ 142800-36-0 ]
  • 7
  • [ 15839-70-0 ]
  • C47H78N4O34 [ No CAS ]
  • C53H88N4O38 [ No CAS ]
  • 8
  • [ 15839-70-0 ]
  • 4-methoxybenzyl O-(3-sulfo-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-2-deoxy-6-O-sulfo-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside disodium salt [ No CAS ]
  • 4-methoxybenzyl O-(3-sulfo-β-D-galactopyranosyl)-(1->4)-O-[(α-L-fucopyranosyl)-(1->3)]-O-(2-acetamido-2-deoxy-6-O-sulfo-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside disodium salt [ No CAS ]
  • 9
  • [ 15839-70-0 ]
  • N-{(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-5-Acetylamino-4,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide [ No CAS ]
  • C28H48N2O20 [ No CAS ]
  • 10
  • [ 15839-70-0 ]
  • C71H115N11O45S2 [ No CAS ]
  • C83H135N11O53S2 [ No CAS ]
  • 11
  • [ 64160-39-0 ]
  • [ 15839-70-0 ]
  • [ 56343-02-3 ]
  • 12
  • [ 15839-70-0 ]
  • [ 156521-67-4 ]
  • 5-Methoxycarbonylhexyl 2-acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside [ No CAS ]
  • 13
  • [ 15839-70-0 ]
  • [ 211746-74-6 ]
  • 5-Methoxycarbonylhexyl 2-acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(3-O-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulo-pyrnuronic acid]-β-D-galactopyranosyl)-β-D-glucopyranoside [ No CAS ]
  • 14
  • [ 15839-70-0 ]
  • Methyl 3,6-di-O-{2-O-[4-O-(β-D-galactopyranosyl)-2-deoxy-2-acetamido-β-D-glucopyranosyl]-α-D-mannopyranosyl}-α-D-mannopyranoside [ No CAS ]
  • Methyl 3,6-di-O-(2-O-[2-acetamido-2-deoxy-3-O-{α-L-fucopyranosyl}-4-O-{β-D-galactopyranosyl}-β-D-glucopyranosyl]-α-D-mannopyranosyl)-α-D-mannopyranoside [ No CAS ]
  • 15
  • [ 15839-70-0 ]
  • Methyl 3,6-di-O-(2-O-[2-acetamido-2-deoxy-4-O-{3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulo-pyranuronic acid)-β-D-galactopyranosyl}-β-D-glucopyranosyl]-α-D-mannopyranosyl)-α-D-mannopyranoside [ No CAS ]
  • Methyl 3,6-di-O-(2-O-[2-acetamido-2-deoxy-3-O-{α-L-fucopyranosyl}-4-O-(3-O-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulo-pyranuronic acid]-β-D-galactopyranosyl)-β-D-glucopyranosyl]-α-D-mannopyranosyl)-α-D-mannopyranoside [ No CAS ]
  • 16
  • [ 15839-70-0 ]
  • N3-Benzyloxycarbonyl-N1-[3,6-bis-O-[(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2,3)-β-D-galactopyranosyl-(1,4)-2-acetamido-2-deoxy-β-D-galactopyranosyl]-β-D-galactopyranosyl]-β-alanine amide [ No CAS ]
  • C79H124N6O52 [ No CAS ]
  • 17
  • N,N'-diacetylchitobiose [ No CAS ]
  • [ 15839-70-0 ]
  • β-D-GlcNAc(1->4)-[α-L-Fuc(1->6)]-D-GlcNAc [ No CAS ]
  • 18
  • Lactose [ No CAS ]
  • [ 15839-70-0 ]
  • 2'-O-fucosyllactose [ No CAS ]
  • 19
  • [ 15839-70-0 ]
  • C35H59N2O24S(1-)*Na(1+) [ No CAS ]
  • C41H69N2O28S(1-)*Na(1+) [ No CAS ]
  • 20
  • [ 15839-70-0 ]
  • [ 177610-59-2 ]
  • C40H70N2O26S [ No CAS ]
  • 21
  • [ 15839-70-0 ]
  • [ 785765-22-2 ]
  • (2S) 3-cyclohexyl-2-O-{1-O-[(1R,2R) 2-O-(α-L-fucopyranosyl)cyclohexyl]β-D-galactopyranos-3-yl}propionic acid [ No CAS ]
  • 23
  • 6-O-β-D-galactopyranosyl-D-galactose [ No CAS ]
  • [ 15839-70-0 ]
  • (3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-tetrahydro-pyran-2,3,4,5-tetraol [ No CAS ]
  • 24
  • N-acetyl-D-lactosamine [ No CAS ]
  • [ 15839-70-0 ]
  • O-(6-Desoxy-α-L-galactopyranosyl)-(1-2)-O-(β-D-galactopyranosyl)-(1-4)-2-acetamido-2-desoxy-D-glucopyranose [ No CAS ]
  • 25
  • [ 20869-27-6 ]
  • [ 15839-70-0 ]
  • C18H32O15 [ No CAS ]
  • 26
  • <β-D-Gal-(1<*>3)>2-β-D-Gal-(1<*>4)-D-Glc [ No CAS ]
  • [ 15839-70-0 ]
  • C30H52O25 [ No CAS ]
  • 27
  • β-D-Galp-(1->3)-β-D-Galp-(1->3)-β-D-Galp-(1->3)-β-D-Galp-(1->4)-D-Glc [ No CAS ]
  • [ 15839-70-0 ]
  • C36H62O30 [ No CAS ]
  • 28
  • β-D-Galp-(1->3)-β-D-Galp-(1->3)-β-D-Galp-(1->3)-β-D-Galp-(1->3)-β-D-Galp-(1->4)-D-Glc [ No CAS ]
  • [ 15839-70-0 ]
  • C42H72O35 [ No CAS ]
  • 29
  • methyl β-D-galactopyranosyl-<1->3>-β-D-galactopyranoside [ No CAS ]
  • [ 15839-70-0 ]
  • [ 613243-53-1 ]
  • 30
  • [ 117895-03-1 ]
  • [ 15839-70-0 ]
  • [ 684237-06-7 ]
  • 31
  • [ 128443-50-5 ]
  • [ 15839-70-0 ]
  • [ 182276-49-9 ]
  • 32
  • [ 144722-08-7 ]
  • [ 15839-70-0 ]
  • (2S,3S,4R,5S,6S)-2-[(2S,3R,4S,5R,6R)-2-((2R,3R,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]
  • 33
  • [ 15839-70-0 ]
  • [ 7216-69-5 ]
  • [ 155911-53-8 ]
  • 34
  • [ 15839-70-0 ]
  • [ 65207-55-8 ]
  • (2S,3S,4R,5S,6S)-2-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-2-((2R,3S,4R)-4-hydroxy-2-hydroxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]
  • 35
  • [ 75669-79-3 ]
  • [ 15839-70-0 ]
  • [ 848566-17-6 ]
  • 36
  • heptakis{6-deoxy-6-S-[7-(2-acetamido-4-O-(3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranosyl-oxy)-4-aza-3-oxo-heptyl]-6-thio}-cyclomaltoheptaose [ No CAS ]
  • [ 15839-70-0 ]
  • heptakis{6-deoxy-6-S-[7-(2-acetamido-4-O-(3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-2-O-(α-D-fucopyranosyl)-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranosyl-oxy)-4-aza-3-oxo-heptyl]-6-thio}-cyclomaltoheptaose [ No CAS ]
  • 37
  • (S)-2-[(2R,3S,4S,5R,6R)-3,5-Dihydroxy-2-hydroxymethyl-6-((1R,2R)-2-hydroxy-1-methyl-propoxy)-tetrahydro-pyran-4-yloxy]-3-phenyl-propionic acid [ No CAS ]
  • [ 15839-70-0 ]
  • (S)-2-{(2R,3S,4S,5R,6R)-3,5-Dihydroxy-2-hydroxymethyl-6-[(1R,2R)-1-methyl-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid [ No CAS ]
  • 38
  • C43H63N3O23 [ No CAS ]
  • [ 15839-70-0 ]
  • C49H73N3O27 [ No CAS ]
  • 39
  • [ 122290-69-1 ]
  • [ 15839-70-0 ]
  • [ 122290-72-6 ]
  • 40
  • [ 122290-73-7 ]
  • [ 15839-70-0 ]
  • [ 122290-74-8 ]
  • 41
  • [ 15839-70-0 ]
  • [ 177610-44-5 ]
  • C41H71N3O25 [ No CAS ]
  • 42
  • [ 15839-70-0 ]
  • [ 177610-49-0 ]
  • C43H72N2O26 [ No CAS ]
  • 43
  • [ 15839-70-0 ]
  • [ 177610-57-0 ]
  • C46H72N2O25 [ No CAS ]
  • 44
  • [ 15839-70-0 ]
  • [ 219484-16-9 ]
  • 8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-deoxy-2-(methyl-β-D-glucohexopyranosyluronamide)-β-D-glucopyranoside [ No CAS ]
  • 45
  • [ 15839-70-0 ]
  • [ 294677-28-4 ]
  • C18H32O11 [ No CAS ]
  • 46
  • [ 15839-70-0 ]
  • [ 888011-02-7 ]
  • (2S) 3-phenyl-2-O-{1-O-[(1R,2R) 2-O-(α-L-fucopyranosyl)cyclohexyl]β-D-galactopyranos-3-yl}propionic acid [ No CAS ]
  • 47
  • [ 15839-70-0 ]
  • [ 786630-44-2 ]
  • (2R) 3-cyclohexyl-2-O-{1-O-[(1R,2R) 2-O-(α-L-fucopyranosyl)cyclohexyl]β-D-galactopyranos-3-yl}propionic acid [ No CAS ]
  • 48
  • [ 904926-03-0 ]
  • [ 15839-70-0 ]
  • 2'-azidoethyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 49
  • [ 904925-99-1 ]
  • [ 15839-70-0 ]
  • 2'-azidoethyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 50
  • [ 904925-99-1 ]
  • [ 15839-70-0 ]
  • 2'-azidoethyl β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 51
  • [ 15839-70-0 ]
  • [ 338971-38-3 ]
  • 2'-azidoethyl β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 52
  • [ 15839-70-0 ]
  • [ 338971-38-3 ]
  • [ 904926-03-0 ]
  • 53
  • [ 15839-70-0 ]
  • [ 485388-17-8 ]
  • 2-azidoethyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulo pyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->4)[(1->3)-α-L-fucopyranosyl]-2-acetamido-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 54
  • C37H37N5O18P2 [ No CAS ]
  • [ 15839-70-0 ]
  • 55
  • [ 15839-70-0 ]
  • [ 730971-20-7 ]
  • <i>N</i>-[6-hydroxymethyl-2-[2-(pyridin-2-ylamino)-ethoxy]-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide [ No CAS ]
  • 56
  • [ 131897-73-9 ]
  • [ 15839-70-0 ]
  • 57
  • [ 140223-15-0 ]
  • [ 15839-70-0 ]
  • 58
  • [ 15839-70-0 ]
  • α-L-Fucp-[α-D-Galp(1->3)](1->2)-β-D-Galp-(1->3)-α-GalpNAc-OMe [ No CAS ]
  • 59
  • [ 15839-70-0 ]
  • (2R,3R,4R,5R)-4-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexane-1,2,3,5,6-pentaol [ No CAS ]
  • 60
  • [ 15839-70-0 ]
  • C34H58N2O25 [ No CAS ]
  • 61
  • [ 15839-70-0 ]
  • C45H75N3O33 [ No CAS ]
  • 62
  • GlcNAcβ(1,4)GlcNAcβ(1,4)GlcNAcβ(1,4)GlcNAcβ(1,4)GlcNAcβ(1,4)GlcNAc [ No CAS ]
  • [ 15839-70-0 ]
  • GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAcβ1-4GlcNAcβ1-4GlcNAcβ1-4GlcNAc [ No CAS ]
YieldReaction ConditionsOperation in experiment
Fuc-TV; at 20.0℃; for 120h; N-Acetyl-chitohexaose (1.0 µmol, 5 mM) was fucosylated with <strong>[15839-70-0]GDP-Fuc</strong>ose (1.0 µmol, 5 mM) and 25 mU Fuc-TV at room temperature for 5 days. MALDI-TOF MS of the purified representative mixture of the product oligosaccharides showed that 31 % of N-acetyl-chitohexaose was fucosylated (Fig. 2B). The product saccharides were further purified in in HPAE-chromatography run isocratically with 40 mM NaOH (Fig 1B). The peak eluting at 7.09 min was pooled, was desalted and was further purified by gel filtration HPLC. The product heptasaccharide (195 nmol) showed in MALDI-TOF analysis 96 % of monofucosylated N-acetyl-chitohexaose, Glycan 6, and 4 % of N-acetyl-chitohexaose, Fig. 2C. The 1D 1H NMR spectrum (Table 2) shows the H1 signals in the GlcNAc5, the GlcNAc6 and the fucose units in Glycan 6, which are nearly identical with their counteparts in Glycan 4. This suggests that the Glycan 6 is GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAcβ1-4GlcNAcβ1-4GlcNAcβ1-4GlcNAc. This notion is further supported by the identical H4-signals of the distal GlcNAc6 units and the fucose H5 resonances in the two glycans. The similarity of this latter pair of signals in the two glycans is particularly significant, because they are known to interact in Glycan 4 (see above), and are likely to be very sensitive to stuctural differences. Likewise, the similarity of fucose H5 signals in Glycan 6, and Glycan 4 speaks for the identity of the nonreducing area in these three saccharides
  • 63
  • chitotriose [ No CAS ]
  • [ 15839-70-0 ]
  • GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAc [ No CAS ]
YieldReaction ConditionsOperation in experiment
Incubation of N-acetyl-chitotriose (1000 nmol, 5 mM) with <strong>[15839-70-0]GDP-fucose</strong> (600 nmol, 3 mM) and 1.4 mU of the enzyme for four days at 37C gave an oligosaccharide mixture. After ion exchange desalting, mild β-N-acetylhexosaminidase treatment, and repeated gel filtration HPLC runs, a sample of 221 nmol of purified fucosylated N-acetyl-chitotriose was obtained. MALDI-TOF MS revealed that the product contained 92 % of fucosylated N-acetyl-chitotriose and 7 % of N-acetyl-chitotriose. The 1D 1H-NMR-spectrum of the product was almost identical with that of Fuc-TV-generated Glycan 3. The ESI-MS-data of the Glycan 3 in reduced form, too, were identical to those obtained with reduced derivative of the Fuc-TV-generated Glycan 3 (not shown).
  • 64
  • chitotriose [ No CAS ]
  • [ 15839-70-0 ]
  • Fuc1GlcNAc2 [ No CAS ]
  • GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAc [ No CAS ]
  • N,N'-diacetylchitobiose [ No CAS ]
YieldReaction ConditionsOperation in experiment
The oligosaccharide mixture, generated by incubation of N-acetyl-chitotriose (1000 nmol, 5 mM) with <strong>[15839-70-0]GDP-Fuc</strong> (1000 nmol, 5 mM) and 25 mU Fuc-TV at room temperature for 5 days was desalted and isolated by gel filtration HPLC. MALDI-TOF-MS revealed that the mixture contained 32 mol % fucosylated N-acetyl-chitotriose and 68 % N-acetyl-chitotriose. This mixture was subjected to the "mild treatment" with jack bean β-N-acetylhexosaminidase, which cleaved most of the surplus N-acetyl-chitotriose substrate but only a small amount of the fucosylated N-acetyl-chitotriose product. A representative sample of all oligosaccharides was isolated from a 5 % aliquot of the digest by using gel filtration HPLC. MALDI-TOF MS analysis of showed that it consisted of fucosylated N-acetyl-chitotriose 67 mol %, N-acetyl-chitotriose 7 %, Fuc1GlcNAc2 12 %, and N-acetyl-chitobiose 13 %. The monofucosylated N-acetyl-chitotriose was purified from the rest of the β-N-acetylhexosaminidase digest by gel filtration HPLC. MALDI-TOF-MS analysis of the purified Fuc1GlcNAc3, Glycan 3, revealed the presence of only a 5 % N-acetyl-chitotriose contamination. The total yield of the purified Glycan 3 was 191 nmol (19 %).
  • 65
  • N,N',N'',N'''-tetraacetylchitotetraose [ No CAS ]
  • [ 15839-70-0 ]
  • GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAc [ No CAS ]
  • GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAcβ1-4GlcNAc [ No CAS ]
  • chitotriose [ No CAS ]
  • N,N'-diacetylchitobiose [ No CAS ]
YieldReaction ConditionsOperation in experiment
8%; 50%; 6% Incubation of N-acetyl-chitotetraose (1000 nmol, 5 mM) with <strong>[15839-70-0]GDP-Fuc</strong> (1000 nmol, 5 mM) and 25 mU human Fuc-TV at room temperature for 5 days, and isolation of the resulting oligosaccharide mixture by using gel filtration HPLC gave a product consisting of 32 mol % fucosylated N-acetyl-chitotetraose and 68 % of unreacted N-acetyl-chitotetraose (Fig. 2A). The mild treatment of the mixture with jack bean β-N-aceylhexosaminidase followed by chromatographic removal of the liberated from GlcNAc gave an oligosaccharide mixture consisting of Fuc1GlcNAc4 50 %, GlcNAc4 6 %, Fuc1GlcNAc3 8 %, GlcNAc3 14 %, GlcNAc2 22 mol %. The composition of this mixture implies that also the fucosylated N-acetyl-chitotetraose was cleaved much slower than N-acetyl-chitotetraose by the β-N-acetylhexosaminidase, confirming the analogous data on degradation of Glycan 3. The oligosaccharide mixture was then fractionated by gel filtration HPLC, yielding a purified product (225 nmol) that consisted of 93 mol % of fucosylated N-acetyl-chitotetraose and 7 % N-acetyl-chitotetraose.
  • 66
  • N,N',N'',N'''-tetraacetylchitotetraose [ No CAS ]
  • [ 15839-70-0 ]
  • GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAcβ1-4GlcNAc [ No CAS ]
YieldReaction ConditionsOperation in experiment
human milk Fuc-Ts; at 37.0℃; for 96h;Conversion of starting material; N-Acetyl-chitotetraose (6.0 µmol, 5 mM), and <strong>[15839-70-0]GDP-Fuc</strong> (3.0 µmol, 2.5 mM) were incubated with 8.7 mU of the enzyme for four days at 37C. After desalting and gel filtration HPLC-run, the fucosylated product was separated from the non-fucosylated N-acetyl-chitotetraose by HPAEC using isocratic run with 40 mM NaOH (not shown). The purified product was desalted by ion exchange and was further purified by gel filtration HPLC yielding 744 nmol monofucosylated N-acetyl-chitotetraose. MALDI-TOF mass spectrometry of the product revealed that it was uncontaminated by N-acetyl-chitotetraose acceptor (not shown).
  • 67
  • Glcβ1-3GalNAcβ1-4Glcβ1-3GalNAcol [ No CAS ]
  • [ 15839-70-0 ]
  • Glcβ1-3GalNAcβ1-4(Fucα1-3)Glcβ1-3GalNAcol [ No CAS ]
YieldReaction ConditionsOperation in experiment
human milk fucosyltransferase(s); Chondroitin sulfate (shark cartilage, Sigma) was cleaved by hyaluronidase (bovine testes, Sigma; chondroitin sulfates can be also cleaved with chondroitinases giving oligosaccharides with delta-uronic acid at non reducing end) to sulfated oligosaccharides such as[GlcAβ1-3(sulf-6)GalNAcβ1-4]nGlcAβ1-3(sulf-6)GalNAc. Fractions containing tetrasaccharide-like materials were purified and desulfated as essentially as described in (41). Tetrasaccharide and hexasaccharide fractions were purified by gel filtration and anion exhange chromatographies. Similar oligosaccharides were also produced by first desulfating and then cleaving by hyaluronidase and purifying the products. The GlcA-residues of the tetrasaccharide were reduced to Glc by EDAC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) and NaBH4. The reduced tetrasaccharide Glcβ1-3GalNAcβ1-4Glcβ1-3GalNAcol was purified and fucosylated using <strong>[15839-70-0]GDP-Fuc</strong> and human milk fucosyltransferase(s). The MALDI-TOF mass spectrometry revealed peaks at m/z 919.8 and m/z 935.8 corresponding to the product Glcβ1-3GalNAcβ1-4(Fucα1-3)Glcβ1-3GalNAcol (calc. m/z [M+Na]+ is 919.7 and m/z [M+K]+ is 935.7).
  • 68
  • GlcNAcylβ1-4GlcNAcβ1-4GlcNAcβ1-4GlcNAc [ No CAS ]
  • [ 15839-70-0 ]
  • GlcNacylβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAcβ1-4GlcNAc [ No CAS ]
YieldReaction ConditionsOperation in experiment
With manganese(ll) chloride;Fuc-TVI; GlcNAcylβ1-4GlcNAcβ1-4GlcNAcβ1-4GlcNAc, wherein Acyl is trans-9-octade-cenoyl, synthesis of the acceptor being described in (13), can be incubated with Fuc-TVI and MnCl2 under conditions described above for Fuc-TVI, but acceptor concentrations between 0.1-0.5 mM are preferred. The product GlcNA-cylβ1-4(Fucα1-3)GlcNAcβ1-4GlcNAcβ1-4GlcNAc is purified chromatographically and analyzed by NMR-spectroscopy and mass spectrometry.
  • 69
  • [ 15839-70-0 ]
  • [ 1093384-59-8 ]
  • 70
  • [ 15839-70-0 ]
  • [ 1093384-61-2 ]
  • 71
  • [ 18186-48-6 ]
  • [ 1093679-47-0 ]
  • [ 15839-70-0 ]
  • 72
  • [ 15839-70-0 ]
  • 3-aminopropyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->3)-α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-galactopyranoside [ No CAS ]
  • 3-aminopropyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->3)-α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside [ No CAS ]
  • 73
  • [ 1246842-76-1 ]
  • [ 15839-70-0 ]
  • β-D-galactopyranosyl-(1→4)-[α-L-fucopyranosyl (1→3)]-2-deoxy-2-acetamido-D-glucopyranosyl-β-1-azidopropane [ No CAS ]
  • 74
  • [ 1340474-27-2 ]
  • [ 15839-70-0 ]
  • C35H47NO17 [ No CAS ]
  • 75
  • [ 75598-07-1 ]
  • [ 15839-70-0 ]
  • C20H35NO15 [ No CAS ]
  • 76
  • 6-deoxy-L-galactose [ No CAS ]
  • Guanosine 5'-triphosphate [ No CAS ]
  • [ 15839-70-0 ]
  • 77
  • C93H153N8O69(1-)*Na(1+) [ No CAS ]
  • [ 15839-70-0 ]
  • α-L-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→3)-(α-L-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6))-β-D-mannopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-D-glucopyranose [ No CAS ]
  • 78
  • [ 446-72-0 ]
  • [ 15839-70-0 ]
  • genistein fucoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium(II) chloride hexahydrate; glycosyltransferase from Arabidopsis thaliana; In aq. buffer; at 37.0℃; for 3h;pH 7.5;Enzymatic reaction; General procedure: After checking the expression of protein, glycosylation reactions were carriedout using crude protein (AtUGT89C1) with genistein and sugars (T/UDP-α-Dglucose,UDP-α-D-galactose, UDP-α-D-glucuronic acid, UDP-α-D-N-acetyl-Dglucosamine,UDP-α-DN-acetylgalactosamine, dTDP-β-L-rhamnose, dTDP-α-2-deoxy-D-glucose, and <strong>[15839-70-0]GDP-β-L-fucose</strong>) as sugar donors. The reaction was carriedout in a total volume of 200 μL containing 100mMTris-HCl (pH 7.5) buffer, 2mMNDP sugar, 2 mM genistein, 10 mM MgCl2. 6H2 O, and 30 μL of crude protein(enzyme concentration was not calculated). The reaction mixtures were incubatedat 37C for 3 h. The reaction mixture lacking enzyme served as the control. Thereactionwas quenched by adding 400 μL chilled methanol and vortexing for severalminutes. Aliquots were centrifuged at 16,000×g to remove denatured proteins, andthe reaction products were monitored by HPLC coupled with a photodiode array(PDA), with 20 μL injected after proper dilution.
  • 79
  • C47H61F17N6O21S [ No CAS ]
  • [ 15839-70-0 ]
  • C53H71F17N6O25S [ No CAS ]
  • 80
  • C47H61F17N6O23S [ No CAS ]
  • [ 15839-70-0 ]
  • C53H71F17N6O27S [ No CAS ]
  • 81
  • C58H78F17N7O31S [ No CAS ]
  • [ 15839-70-0 ]
  • C64H88F17N7O35S [ No CAS ]
  • 82
  • [ 15839-70-0 ]
  • [ 209671-46-5 ]
  • C26H46N4O15 [ No CAS ]
  • 83
  • C58H78F17N7O29S [ No CAS ]
  • [ 15839-70-0 ]
  • C64H88F17N7O33S [ No CAS ]
  • 84
  • [ 1609290-86-9 ]
  • [ 15839-70-0 ]
  • C37H63N5O23 [ No CAS ]
  • 85
  • C61H84F17N7O31S [ No CAS ]
  • [ 15839-70-0 ]
  • C73H104F17N7O39S [ No CAS ]
  • 86
  • Nα-9-fluorenylmethyloxycarbonyl-O-{2-acetamido-2-deoxy-β-glucopyranosyl-(1→2)-[β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl]-(1→6)-α-D-mannopyranosyl}-L-threonine [ No CAS ]
  • [ 15839-70-0 ]
  • C53H75N3O29 [ No CAS ]
  • 87
  • Nα-9-fluorenylmethyloxycarbonyl-O-{β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-[2-acetamido-2-deoxy-β-glucopyranosyl-(1→6)]-α-D-mannopyranosyl}-L-threonine [ No CAS ]
  • [ 15839-70-0 ]
  • C53H75N3O29 [ No CAS ]
  • 88
  • C39H52N2O20 [ No CAS ]
  • [ 15839-70-0 ]
  • C45H62N2O24 [ No CAS ]
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