ライフサイエンスコーパス: pentasaccharide

1 saccharide, trisaccharides type 2 and 6, and pentasaccharide).

2 studied in both the absence and presence of pentasaccharide.

3 e P-helix formation and ATIII binding to the pentasaccharide.

4 ecific ionic and non-ionic contacts with the pentasaccharide.

5 ) only approximately 2-fold tighter than the pentasaccharide.

6 t (k(2)) in both the absence and presence of pentasaccharide.

7 is more buried and fits more snugly than the pentasaccharide.

8 ed in more hydrophobic interactions than the pentasaccharide.

9 had a 5-fold higher affinity for heparin and pentasaccharide.

10 hter complex with the trisaccharide than the pentasaccharide.

11 contacts with all the sugar residues of the pentasaccharide.

12 t (k(2)) in both the absence and presence of pentasaccharide.

13 ithrombin activated by high affinity heparin pentasaccharide.

14 is also established after exposing the core pentasaccharide.

15 interactions with high affinity heparin and pentasaccharide.

16 antibodies recognizing the C. difficile PS-I pentasaccharide.

17 n make contact with a single heparin-derived pentasaccharide.

18 ay or S-layer protein is glycosylated with a pentasaccharide.

19 of AT in the absence and in the presence of pentasaccharide.

20 ning oligosaccharides, a trisaccharide and a pentasaccharide.

21 inked lattices between SBA and four isomeric pentasaccharides.

22 factor for the syntheses of oligomers beyond pentasaccharides.

23 isaccharides 17, 18, tetrasaccharide 23, and pentasaccharide 26.

24 antithrombin by a sequence-specific heparin pentasaccharide (300-500-fold), (ii) allosteric activati

25 by complexation with a high-affinity heparin pentasaccharide abolished the serpin's ability to inhibi

26 ated protein C mutant, similar to factor Xa, pentasaccharide accelerated the reaction 375-fold.

27 A sequence-specific heparin pentasaccharide activates the serpin, antithrombin, to i

28 y wild-type reactivities with thrombin after pentasaccharide activation as well as normal full-length

29 However, heparin pentasaccharide activation increased the reactivity of t

30 up functions as a key determinant of heparin pentasaccharide activation of antithrombin both by contr

31 ts reactivity with these proteases following pentasaccharide activation.

32 Pentasaccharide addition elicited no further activation

33 The active AT-binding pentasaccharide also accelerated the inactivation rates

34 R129H and R129Q antithrombins bound pentasaccharide and full-length heparins containing the

35 eparin and 33- to 70-fold in the presence of pentasaccharide and full-length heparins.

36 x D-sheet A interface, adjacent to the ATIII pentasaccharide and heparin cofactor-binding sites and s

37 Using pentasaccharide and hexasaccharide model compounds, we s

38 of the biologically important ATIII binding pentasaccharide and its precursors, which differ from ea

39 syl donors allowed for the completion of the pentasaccharide and provides a synthetic strategy that i

40 4Gal-T1) in complex with a GlcNAc-containing pentasaccharide and several GlcNAc-containing trisacchar

41 The serum binds both the defucosylated pentasaccharide and the fucosylated hexasaccharide witho

42 ) NMR of the complex consisting of the HNK-1 pentasaccharide and the HNK-1 412 antibody.

43 Multiple pentasaccharide and trisaccharide side chains are O link

44 s of h-M340H-beta4Gal-T1 in complex with the pentasaccharide and various trisaccharides at 1.9-2.0A r

45 ut the total syntheses of heparosan tri- and pentasaccharides and heparin di-, tetra-, hexa-, and oct

46 d antD resulted in the disappearance of BclA pentasaccharides and the appearance of a tetrasaccharide

47 This is demonstrated for two isomeric pentasaccharides and two isomeric hexasaccharides, each

48 The H-type II pentasaccharide, Le(x) pentasaccharide, and Le(y) hexasaccharide were prepared

49 tols, 3,6-disubstituted mannitol-terminating pentasaccharides, and 2-mono- and 2,6-disubstituted mann

50 , four isomeric trisaccharides, two isomeric pentasaccharides, and two isomeric hexasaccharides) as t

51 gest that PAA binds antithrombin in both the pentasaccharide- and the extended heparin-binding sites,

52 These enzymes are the target of the pentasaccharide antibiotic moenomycin as well as the pro

53 structure with that of the complex with the pentasaccharide antigen [-->2)-alpha-L-Rha-(1-->2)-alpha

54 ues implicated in the binding of the heparin pentasaccharide (Arg47, Lys114, Lys125, Arg129) provides

55 ith biomedical importance, i.e., polyanionic pentasaccharide Arixtra and polycationic peptide protami

56 ch chemokine pair was mixed with the heparin pentasaccharide, Arixtra, and assayed by ESI-FTICR mass

57 de, sucrose octasulfate, and an octasulfated pentasaccharide, Arixtra.

58 This S-layer is glycosylated with the same pentasaccharide as that of Hfx. volcanii, but the intact

59 The key building block, a pentasaccharide-Asn analogue containing two thiol residu

60 binding of the terminal Gal residues of the pentasaccharides at identical sites in each monomer, wit

61 nicellular eukaryotes, Skp1 is modified by a pentasaccharide attached to a hydroxyproline near its C

62 ther protists, Skp1 is regulated by a unique pentasaccharide attached to hydroxylated Pro-143 within

63 Skp1 hydroxyproline is modified by a similar pentasaccharide, based on mass spectrometry, and that as

64 found the complex-type N-linked glycan core pentasaccharide beta-GlcNAc-(1-->2)-alpha-Man-(1-->3)-[b

65 ng-end residue D produced variable losses in pentasaccharide binding energy of approximately 15-75% b

66 The salt dependence of pentasaccharide binding showed that the binding defect o

67 , the designed activators do not bind in the pentasaccharide binding site in antithrombin resulting i

68 nd Lys139, which are outside of the putative pentasaccharide binding site, play pivotal roles in the

69 haride ligand that binds antithrombin in the pentasaccharide binding site, while it competes with ful

70 ion for R132 and K133 peripheral to the main pentasaccharide binding site.

71 to 24%) and in the association constant for pentasaccharide binding to antithrombin [(2.6 +/- 0.3)-f

72 Pentasaccharide binding ultimately results in a conforma

73 f the combining site groove much better than pentasaccharide binding.

74 indicate that sulfated DHPs bind to both the pentasaccharide-binding site and extended heparin-bindin

75 n native ATIII and then becomes exposed when pentasaccharide binds to the inhibitor and activates it.

76 The results show a pentasaccharide bound across the catalytic site of MalP

77 n a native-like state in spite of having the pentasaccharide bound in the normal fashion.

78 ed non-natural disaccharide acceptor, into a pentasaccharide building block suitable for chain elonga

79 sugar that can be subsequently extended to a pentasaccharide by novel glycosyltransferases.

80 at contributes the 2nd and 3rd sugars of the pentasaccharide cap formed on Skp1 hydroxyproline.

81 1000- and 2-fold faster, respectively, than pentasaccharide-catalyzed rates.

82 On the other hand, the pentasaccharide-catalyzed reactivity of antithrombin wit

83 at proline 143, which is then modified by a pentasaccharide chain.

84 Recent determination of the structure of the pentasaccharide complex found a glycosidic linkage psi t

85 -ray cocrystal structure of the antithrombin-pentasaccharide complex shows that Trp49 does not contac

86 a recent X-ray structure of the antithrombin-pentasaccharide complex, suggested that the majority of

87 While the 2,4-, 3,6-, and 2,6-pentasaccharide complexes possess a common P6422 space g

88 No activation was observed, even at a pentasaccharide concentration 10 times higher than that

89 ictyostelium, Skp1 is modified by an unusual pentasaccharide containing a Galalpha1-Fuc linkage, whos

90 Lactoseries tetrasaccharide c (LSTc), a pentasaccharide containing a terminal alpha2,6-linked si

91 olysaccharide, which consists of a repeating pentasaccharide containing d-mannose, d-glucose and l-rh

92 ytic site of dGMII led to the synthesis of a pentasaccharide containing the alpha(1,6)-linked Man of

93 Lacto-N-fucopentaose III (LNFPIII) is a pentasaccharide containing the Lewis(x) trisaccharide th

94 n of antA resulted in the appearance of BclA pentasaccharides containing anthrose analogs possessing

95 e the synthesis of unnatural 6-O-sulfated CS pentasaccharides containing either a 6-O-sulfo-2-azidoga

96 ractions, suggesting that Arg(129) binds the pentasaccharide cooperatively with other residues.

97 ruption ofmanBcoregives rise to a deep-rough pentasaccharide core (beta-d-Glcp-(1-->4)-alpha-Kdop-(2-

98 iantennary structures with a common N-linked pentasaccharide core (mannose3-N-acetylglucosamine2), mo

99 y removing sugars outside the N-glycopeptide pentasaccharide core with exoglycosidases.

100 serpin allosterically activated by a heparin pentasaccharide could be enhanced as much as 55-fold by

101 The 2, 3-pentasaccharide cross-linked complex, on the other hand,

102 vation of the serpin antithrombin by heparin pentasaccharide DEFGH was previously shown to involve tr

103 de unit DEF of the sequence specific heparin pentasaccharide DEFGH.

104 molecules devoid of the antithrombin-binding pentasaccharide DEFGH.

105 al saccharide residues of a specific heparin pentasaccharide, denoted DEFGH, in the allosteric activa

106 ents heparin binding to FXa, the heparin and pentasaccharide dependence of FXa inactivation by AT in

107 pentasaccharide with negligible transfer to pentasaccharides derived from hyaluronan or heparan.

108 ions in an AglB-dependent manner by the same pentasaccharide detected on H. volcanii flagellins.

109 B-pentamer with the ganglioside GM1 receptor pentasaccharide diffract to near-atomic resolution.

110 This pentasaccharide drives Th2-type responses in vivo and in

111 N-sulfoglucosamine (GlcNS) and the synthetic pentasaccharide drug fondaparinux demonstrate the broad

112 nally activating antithrombin with a heparin pentasaccharide enhanced the affinity of the serpin for

113 n contrast to thrombin, an active AT-binding pentasaccharide enhanced the inhibition of des-PPW appro

114 Competitive binding studies with heparin pentasaccharide, epicatechin sulfate, and full-length he

115 In all three complexes the pentasaccharide exhibits an altered conformation across

116 Antithrombin binds to specific pentasaccharides expressed on heparin, glycosaminoglycan

117 Frequently, the pentasaccharide fondaparinux is used off-label.

118 lar-weight heparin, and none formed with the pentasaccharide fondaparinux sodium.

119 low-molecular-weight heparin (LMWH), and the pentasaccharide fondaparinux.

120 es for two GAG model compounds, a heparin/HS pentasaccharide (fondaparinux sodium; FX) and enzymatica

121 ude low-molecular-weight heparins (LMWHs); a pentasaccharide (fondaparinux); oral anticoagulants: vit

122 r results showed that GAG model compounds, a pentasaccharide (fondaparinux, FX) and an octasaccharide

123 anti-FXa activity compared with those of the pentasaccharide, fondaparinux, and low molecular weight

124 w molecular weight heparin and the synthetic pentasaccharide, fondaparinux, had similar platelet-pote

125 afts were continuously infused with alphaGal pentasaccharide for 4-5 hr, maintaining the serum oligos

126 The pentasaccharide fragment alpha-d-Man-(1 --> 5)-[alpha-d-

127 formation unless it is activated by a unique pentasaccharide fragment of heparin (H(5)).

128 It has been demonstrated that a unique pentasaccharide fragment of heparin (H5) activates AT by

129 A unique pentasaccharide fragment of heparin can enhance the reac

130 A unique pentasaccharide fragment of high-affinity heparin activa

131 s of two novel tetrasaccharide and two novel pentasaccharide fragments of the Le(a)Le(x) TACA: the te

132 t the synthesis of a tetrasaccharide and two pentasaccharide fragments of the Le(a)Le(x) tumor-associ

133 It was unexpected that pentasaccharide fragments were also detected among the d

134 y steps in the total synthesis of a branched pentasaccharide from a saponin natural product.

135 ate that the nonreducing-end residues of the pentasaccharide function both to recognize the native lo

136 n that is post-translationally modified by a pentasaccharide, Gal alpha1,Gal alpha1,3Fuc alpha1,2Gal-

137 isaccharide (Galalpha1-3Galbeta1-4GlcNAc) or pentasaccharide (Galalpha1-3Galbeta1-4GlcNAcbeta1-3Galbe

138 Dictyostelium, Skp1 is modified by a linear pentasaccharide, Galalpha1-6Galalpha1-Fucalpha1-2Galbeta

139 ata to determine the solution structure of a pentasaccharide, GalNAc6S(beta1-4)GlcA(beta1-3)GalNAc4S(

140 The oligosaccharides used were: pentasaccharide GlcNAcbeta1,2-Manalpha1,6 (GlcNAcbeta1,2

141 binding interactions among CCL7, Arixtra (a pentasaccharide glycosaminoglycan [GAG] analog), and dis

142 The syntheses of the targeted pentasaccharide have been performed with both three- and

143 mic data demonstrate that the native tri- to pentasaccharides have free energies of binding in the ra

144 on sites are modified with covalently linked pentasaccharides having the same mass as that modifying

145 interaction with the negatively charged GD2-pentasaccharide headgroup.

146 parin enoxaparin (Lovenox) and the synthetic pentasaccharide heparin analog fondaparinux (Arixtra), w

147 The binding of pentasaccharide heparin to antithrombin induces a confor

148 iant) inhibits thrombin 17 times faster than pentasaccharide heparin-activated antithrombin.

149 ed and derivatized with a potentially linear pentasaccharide, Hex-->Hex-->Fuc-->Hex-->HexNAc-->(HyPro

150 3)-galactose epitopes were prepared, and the pentasaccharide HNK-1 required incorporation of a 3-O-su

151 In contrast, the fifth sugar of the pentasaccharide, identified as mannose in this study, is

152 The fully protected antithrombotic pentasaccharide idraparinux was synthesized in 23 steps

153 ently assembled the antithrombin III-binding pentasaccharide in just 6 steps, in contrast to the appr

154 he extent of the rate-accelerating effect of pentasaccharide in the AT inhibition of the mutants was

155 tacts (approximately 75) with the Fab as the pentasaccharide, including the same number of hydrogen b

156 es are similar to the value measured for GM1 pentasaccharide, indicating that neither the ceramide mo

157 Binding of GSG4 is identical to the natural pentasaccharide, indicating that the inactive thio compo

158 or activation of factor Xa inhibition is the pentasaccharide-induced conformational change, with appr

159 loss in binding energy for the antithrombin-pentasaccharide interaction due to the disruption of a c

160 inding partner of this group on antithrombin-pentasaccharide interactions by equilibrium binding and

161 eover, we describe the successful use of the pentasaccharide intermediate in the [5 + 5] synthesis of

162 xcept for the ultimate stage, where a single pentasaccharide intermediate is converted into a set of

163 ,6-mannosylation, to form the first branched pentasaccharide intermediate of the pathway.

164 Deprotection of the pentasaccharide intermediate to give the hexyl and amino

165 Herein, the GM1 pentasaccharide is dissected into smaller fragments to d

166 Although distortion of the pentasaccharide is significant, the principal factor in

167 The resulting pentasaccharide is suitably protected for further chain

168 ide as that of Hfx. volcanii, but the intact pentasaccharide is synthesized on a single carrier molec

169 in chains, including the minimal AT-specific pentasaccharide, is mediated exclusively through the all

170 s the additional 6 arm GlcNAc present in the pentasaccharide, it does not serve as a key recognition

171 matic synthesis of the dolichylpyrophosphate pentasaccharide, it was thus possible to define the bioc

172 JCPyV infection of host cells requires the pentasaccharide lactoseries tetrasaccharide c (LSTc) and

173 The H-type II pentasaccharide, Le(x) pentasaccharide, and Le(y) hexasa

174 high-affinity heparin, high-affinity heparin pentasaccharide, long-chain low-affinity heparin, and de

175 nalogues with distinct topological profiles, pentasaccharides LSTa (alpha-2,3 linkage) and LSTc (alph

176 s of epimeric disaccharides and the branched pentasaccharide Man3 glycan, demonstrating that this tec

177 stal structures of MVL free and bound to the pentasaccharide Man3GlcNAc2 at 1.9- and 1.8-A resolution

178 hat the alpha-linked mannose residues in the pentasaccharide Man3GlcNAc2 core was essential to mainta

179 onality could be readily introduced at the N-pentasaccharide (Man3GlcNAc2) core by use of azido-conta

180 and meanwhile preserving the natural, core N-pentasaccharide (Man3GlcNAc2) structure in the resulting

181 Sulfated pentasaccharide may be sufficient to bind to CTX.

182 stitution at lysine 139 had no effect on the pentasaccharide-mediated activation of ATIII toward fact

183 nstrate a pivotal role for lysine 114 in the pentasaccharide-mediated activation of ATIII.

184 e potential role(s) of these residues in the pentasaccharide-mediated activation of ATIII.

185 tion of antithrombin was not affected by the pentasaccharide modifications.

186 tion mechanism was investigated with variant pentasaccharides modified in the GH disaccharide.

187 radation system to recognize the common core pentasaccharide motif (Man3GlcNAc2) of N-linked glycopro

188 ts comprising the first four subunits of the pentasaccharide N-linked to the S-layer glycoprotein, a

189 of the polymer was identified as a branched pentasaccharide of the structure shown.

190 viously investigated the binding of tri- and pentasaccharides of N-glycan with a GlcNAc at their nonr

191 or the fucose at the Le(x) reducing end; the pentasaccharides only lack the galactose residue at the

192 n factor Xa specificity due to activation by pentasaccharide or bridging heparins.

193 an important role in the binding of heparin pentasaccharide or in the mechanism of heparin activatio

194 The four pentasaccharides possess the common structure of (beta-L

195 All variant pentasaccharides produced a normal enhancement of antith

196 nformational preorganization of the branched pentasaccharide rather than through the effect of cooper

197 Concise syntheses of the acidic pentasaccharide, related to the O-antigenic polysacchari

198 th 9V and 9A PS are composed of an identical pentasaccharide repeat unit, as reported previously.

199 The synthetic PS-I pentasaccharide repeating unit as well as the Rha-(1-->3

200 PS A2 consists of a pentasaccharide repeating unit containing mannoheptose,

201 genes are involved in sialic acid synthesis, pentasaccharide repeating unit formation, and oligosacch

202 mproved chemical synthesis protocols for the pentasaccharide repeating unit of PS-I and oligosacchari

203 -antithrombin and alpha-antithrombin+heparin pentasaccharide reported to date (2.6A and 2.9A resoluti

204 ithrombin, we studied the effect of deleting pentasaccharide residues on this activation.

205 tion and previously assigned roles in adding pentasaccharide residues one to four, the composition of

206 a tetrasaccharide comprising the first four pentasaccharide residues.

207 rombin induced by binding a specific heparin pentasaccharide result in very large increases in the ra

208 al activation of the chimeras with a heparin pentasaccharide resulted in normal approximately 100-300

209 t with the altered affinities of the variant pentasaccharides resulting mostly from perturbed interac

210 ite this affinity loss, the 3-O-desulfonated pentasaccharide retained the ability to induce tryptopha

211 s two complexes with two antigen segments (a pentasaccharide Rha A-Rha B-Rha C-GlcNAc D-Rha A' and a

212 e strongly associated to the presence of the pentasaccharide sequence AGA*IA (A(NAc,6S)-GlcUA-A(NS,3,

213 antithrombin, by binding through a specific pentasaccharide sequence containing a critical 3-O-sulfo

214 it mechanism to bind with high affinity to a pentasaccharide sequence found in about one-third of hep

215 Activation occurs upon binding of a specific pentasaccharide sequence found in heparin that results i

216 s establish an important role of the heparin pentasaccharide sequence in preferential binding and sta

217 AT-III binding to a specific heparin pentasaccharide sequence, containing an unusual 3-O sulf

218 alized sensor for the physiologically active pentasaccharide sequence.

219 tope becomes larger across the tri-, tetra-, pentasaccharide series, entropy contributions to the fre

220 ical evidence for conventional Hbonds in the pentasaccharide sialyl Lewis-X (sLe(X)-5) between 5 and

221 The nonreducing terminal residue of the pentasaccharide side chain is the unusual sugar anthrose

222 llagen-like region with multiple copies of a pentasaccharide side chain.

223 rase that attaches the fourth residue of the pentasaccharide side chain.

224 or cooperative interactions with the heparin pentasaccharide so as to lock the serpin in the activate

225 ng oligosaccharide acceptors indicate that a pentasaccharide, such as N-glycans with GlcNAc at their

226 P1 is variably modified by an unusual linear pentasaccharide, suggesting the localization of a novel

227 The pentasaccharide terminates with the unusual deoxyamino s

228 To that end, we describe a core pentasaccharide that at potential branching positions is

229 se III (LNFPIII) is a biologically conserved pentasaccharide that contains the Lewis(x) trisaccharide

230 cinetobacter baumannii 17978 revealed that a pentasaccharide that decorates glycoproteins is formed o

231 ) is a structurally homogeneous ULMW heparin pentasaccharide that is synthesized through a lengthy ch

232 st to unfractionated heparin, this synthetic pentasaccharide that mimics the unique Antithrombin III

233 complex of beta4Gal-T1 with I-antigen analog pentasaccharide, the beta1-6-branched GlcNAc moiety is b

234 antithrombin in the absence and presence of pentasaccharide, the difference in reactivity was increa

235 In the case of the 3,6- and 2,6-pentasaccharides, the symmetry of their cross-linked lat

236 old when the serpin was activated by heparin pentasaccharide, thereby transforming antithrombin into

237 22 and Phe-121 make minimal contact with the pentasaccharide, they play a critical role in heparin bi

238 he targets included one tetrasaccharide, one pentasaccharide, three octasaccharides, and two nonasacc

239 esC) but was fully stabilized by the heparin pentasaccharide (Tm 71.8, normal 71.0 degreesC), indicat

240 Global deprotection afforded the target pentasaccharide to be used for the conversion into neogl

241 sulfo group affected both the ability of the pentasaccharide to recognize native antithrombin and its

242 ng geometry of the sequence-specific heparin pentasaccharide to within 2.5 A.

243 Three pentasaccharides, two tetrasaccharides, and a trisacchar

244 The pentasaccharide unit -Man3GlcNAc2- lies at the protein-j

245 The type 9V capsule consists of repeating pentasaccharide units linearly arranged, with an average

246 protected H-type II blood group determinant pentasaccharide utilizing glycosyl phosphate and glycosy

247 cells grown in low salt, substantially less pentasaccharide was detected.

248 ority of the enhanced affinity of the latter pentasaccharide was due to direct electrostatic and hydr

249 (-1) while that for binding to soluble GM(1)-pentasaccharide was found to be approximately 4 x 10(6)

250 The protected chlorohexyl glycoside pentasaccharide was the precursor to the hexyl glycoside

251 peptides carrying two N-linked core tri- and pentasaccharides was achieved.

252 132M and K133M variants to the high affinity pentasaccharide were weakened only 2.3- and 4.5-fold res

253 Pentasaccharides were more stable to heat treatment than

254 tamide was fully reduced to an acetamide the pentasaccharides were obtained in four and five steps, r

255 All of these pentasaccharides were well-resolved and characterized by

256 Fondaparinux is a synthetic pentasaccharide, which binds to antithrombin, thereby in

257 hrombin in a manner identical to the natural pentasaccharide, while a novel hexasaccharide bound the

258 oprotein Asn-13 and Asn-83 are modified by a pentasaccharide, while dolichol phosphate is modified by

259 structure, common to all chloroviruses, is a pentasaccharide with a beta-glucose linked to an asparag

260 affected the preferential interaction of the pentasaccharide with activated antithrombin.

261 unts of GlcA residues to chondroitin-derived pentasaccharide with negligible transfer to pentasacchar

262 w significant binding to the singly branched pentasaccharide with the structure alpha-L-Rhap(1-->2)al

263 In Dictyostelium, Skp1 is modified by a pentasaccharide with the type I blood group H antigen (F

264 glycosidic linkages extending from the core pentasaccharide with thioethers amenable to construction

265 We also detected di-, tri-, and pentasaccharides with one sulfate group.

266 ates as a pentamer with a series of divalent pentasaccharides with terminal LacNAc residues.