Abstract:
:To reveal the function of the carbohydrate portion of glycopeptides and glycoproteins, we chemo-enzymatically synthesized artificially N-glycosylated derivatives of eel calcitonin and studied their three-dimensional structure and biological activity. The CD and NMR spectra in trifluoroethanol-H(2)O solution showed that the glycosylation did not change the three-dimensional structure. All the derivatives retained the strong in vivo hypocalcemic activity of calcitonin. However, the relative activity was dependent on the structure of the attached carbohydrate. The single GlcNAc attachment best enhanced the activity, while larger carbohydrates decreased the activity. This relative activity order of compounds could be partly explained by their calcitonin-receptor binding affinity, though the affinity of the GlcNAc derivative did not exceed that of calcitonin. The enhanced hypocalcemic activity of the GlcNAc derivative was explained by its altered biodistribution. The GlcNAc attachment caused calcitonin to escape from the trap at the liver during the early circulation. Thus, the glycosylation was shown to modulate the biological activity of calcitonin depending on the carbohydrate structure without a change in the peptide backbone conformation.
journal_name
Glycoconj Jjournal_title
Glycoconjugate journalauthors
Tagashira M,Tanaka A,Hisatani K,Isogai Y,Hori M,Takamatsu S,Fujibayashi Y,Yamamoto K,Haneda K,Inazu T,Toma Kdoi
10.1023/a:1016082017366subject
Has Abstractpub_date
2001-06-01 00:00:00pages
449-55issue
6eissn
0282-0080issn
1573-4986journal_volume
18pub_type
杂志文章abstract::Oral exposure to lectins or the presence or absence of bacteria in the rat small intestine were shown by histological methods using anti-lectin antibodies or digoxigenin-labelled lectins to have major effects on the state of glycosylation of lumenal membranes and cytoplasmic glycoconjugates of epithelial cells. Taken ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731865
更新日期:1995-02-01 00:00:00
abstract::UDP-GlcNAc:Man alpha 1-3R beta 1-2-N-acetylglucosaminyltransferase I (GlcNAc-T I; EC 2.4.1.101) catalyses the conversion of [Man alpha 1-6(Man alpha 1-3)Man alpha 1-6][Man alpha 1-3]Man beta-O-R to [Man alpha 1-6(Man alpha 1-3)Man alpha 1-6] [GlcNAc beta 1-2Man alpha 1-3]Man beta-O-R (R = 1-4GlcNAc beta 1-4GlcNAc- Asn...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731234
更新日期:1995-12-01 00:00:00
abstract::Lubrication of mammalian joints is mediated by lubricin, a product of megakaryocyte stimulating factor gene (MSF; GenBank accession #U70136) expression. Lubricin (M(r) approximately 240 kDa) is a mucinous glycoprotein which is 50% (w/w) post-translationally modified with beta(1-3)Gal-GalNAc incompletely capped with Ne...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1021159619373
更新日期:2001-10-01 00:00:00
abstract::Sialosyl-Le(x) (SLex) and its positional isomer sialosyl-Le(a) are the epitopes recognized by the lectin domain of E- and P-selectins. Expression of SLex in polymorphonuclear leukocytes (PMN) plays an important role in recruitment of these cells at sites of inflammation through activation of selectins. We studied expr...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731223
更新日期:1994-06-01 00:00:00
abstract::Colominic acid is an alpha2,8-linked sialic acid polymer produced by Escherichia coli. We found that synthetic sulfated-colominic acids (SC) remarkably inhibited the cytotoxicity of bee and snake venom toward mouse fibroblast cells, but colominic acids showed no inhibition themselves, indicating the important role of ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1007074410201
更新日期:1999-08-01 00:00:00
abstract::Grifola frondosa is an important fungal research resource. However, there was little report about hyperglycemic activity of Grifola frondosa polysaccharide on insulin resistance in vitro. In this study, the hypoglycemic activity of a polysaccharide obtained from Grifola frondosa (GFP) on HepG2 cell and hpyerglycemic m...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-014-9526-x
更新日期:2014-07-01 00:00:00
abstract::The N-glycans from soluble extracts of ten pollens were examined. The pyridylaminated oligosaccharides derived from these sources were subject to gel filtration and reverse-phase HPLC, in conjunction with exoglycosidase digests, and in some cases matrix-assisted laser desorption-ionisation mass spectrometry. In compar...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006960401562
更新日期:1998-11-01 00:00:00
abstract::The conformational space of methyl 6-O-[(R)- and (S)-1-carboxyethyl]-alpha-D-galactopyranoside has been investigated. A grid search employing energy minimization at each grid point over the three major degrees of freedom, namely phi, psi and omega, identified low energy regions. The R-isomer shows five low energy conf...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1018527129939
更新日期:1997-12-01 00:00:00
abstract::UDP-GlcNAc:alpha3-D-mannoside beta1,2- N -acetylglucosaminyltransferase I (GnTI; EC 2.4.1.101) is a Golgi-resident glycosyltransferase that is essential for the processing of oligomannose to hybrid and complex N-glycans in higher eukaryotes. The cDNA of Nicotiana tabacum GnTI has been cloned and characterised previous...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/B:GLYC.0000045099.29038.04
更新日期:2004-01-01 00:00:00
abstract::Multidisciplinary approaches by a number of investigators have established that cell-surface carbohydrates are integral components of recognition systems regulating survival, migration, adhesion, growth and differentiation of various cells. Our own experience and contributions to this exciting field are described. We ...
journal_title:Glycoconjugate journal
pub_type: 传,历史文章,杂志文章
doi:10.1023/a:1011078627247
更新日期:2000-07-01 00:00:00
abstract::As part of our ongoing program aimed at understanding the structural significance of GlcNAcβAsn linkage conserved in all eukaryotic N-glycoproteins, the present study reports on the synthesis and X-ray crystal structures of N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)acetamide (Glc3NAcβNHAc) and the corresponding propio...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-011-9357-y
更新日期:2011-12-01 00:00:00
abstract::Based on the O-specific polysaccharides of the lipopolysaccharides (O-polysaccharides, O-antigens), strains of a clonal species Escherichia coli are classified into 184 O serogroups. In this work, structures of the O-polysaccharides of E. coli O69 and O146 were elucidated and gene clusters for their biosynthesis were ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-016-9730-y
更新日期:2017-02-01 00:00:00
abstract::A major impediment in the analysis of glycosaminoglycans is the difficulty to cleave quantitatively the glycosidic bonds because of the stabilisation of glycosidic bonds and of the relative instability of the liberated constituents. This manuscript describes a modified procedure of methanolysis in the presence of bari...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1007076900562
更新日期:1999-10-01 00:00:00
abstract::Podocalyxin (PC) was first identified as a heavily sialylated transmembrane protein of glomerular podocytes. Recent studies suggest that PC is a remarkable glycoconjugate that acts as a universal glyco-carrier. The glycoforms of PC are responsible for multiple functions in normal tissue, human cancer cells, human embr...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/s10719-016-9757-0
更新日期:2017-04-01 00:00:00
abstract::We have previously shown that murine resident peritoneal macrophages (PEMs) are activated in response to uptake of oligomannose-coated liposomes (OMLs), leading to production of interleukin (IL)-12. To understand the mechanism of activation of PEMs by OMLs, in the present study we investigated the role of a mannose-bi...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-010-9298-x
更新日期:2010-07-01 00:00:00
abstract::Mammalian sulfoglycolipids are comprised of two major members, sulfatide (SO(3)-3Gal-ceramide) and seminolipid (SO(3)-3Gal-alkylacylglycerol). Sulfatide is abundant in the myelin sheath and seminolipid is expressed on the spermatogenic cells. Cerebroside sulfotransferase (CST)-deficient mice generated by gene targetin...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1023/B:GLYC.0000043749.06556.3d
更新日期:2004-01-01 00:00:00
abstract::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-Ga...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9117-9
更新日期:2008-10-01 00:00:00
abstract::Heteropolysaccarides were isolated from the Korean medicinal plant, Phellodendri cortex (Hwangbek), by hot water and alkali extractions. The extracted polysaccharides were fractionated into eight fractions and they are mainly composed of D-N-acetylglucosamine, D-galactose, D-mannose, and D-glucose. Among the polysacch...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1007084506071
更新日期:1999-03-01 00:00:00
abstract::Filamentous fungi are commonly used in the fermentation industry for large scale production of glycoproteins. Several of these proteins can be produced in concentrations up to 20-40 g per litre. The production of heterologous glycoproteins is at least one or two orders of magnitude lower but research is in progress to...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1023/a:1026436424881
更新日期:1999-02-01 00:00:00
abstract::Recently, we demonstrated that the human xylosyltransferase II (XT-II) has enzymatic activity and is able to catalyze the initial and rate-limiting step in the biosynthesis of glycosaminoglycans (GAGs) like chondroitin and dermatan sulfate, as well as heparan sulfate and heparin. Therefore, this enzyme also very likel...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-012-9439-5
更新日期:2013-04-01 00:00:00
abstract::A gene encoding a putative sialidase was identified in the genome of the opportunistic fungal pathogen, Aspergillus fumigatus. Computational analysis showed that this protein has Asp box and FRIP domains, it was predicted to have an extracellular localization, and a mass of 42 kDa, all of which are characteristics of ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-010-9299-9
更新日期:2010-07-01 00:00:00
abstract::O-Glycopyranosyl-N-hydroxysuccinimides of glucose and lactose have been synthesized. Peracetylated sugars, acetobromo sugars and benzoylated thioethyl glycosides have been used as precursors. With boron trifluoride etherate in dichloromethane, peracetylated sugars gave predominantly the beta anomer. Trimethylsilyl tri...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00780758
更新日期:1992-06-01 00:00:00
abstract::Transmannosylation from mannotriose (Man beta 1-4Man beta 1-4Man) to the 4-position at the nonreducing end N-acetylglucosaminyl residue of N,N'-diacetylchitobiose was regioselectively induced through the use of beta-D-mannanase from Aspergillus niger. The enzyme formed the trisaccharide Man beta 1-4GlcNAc beta 1-4GlcN...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731150
更新日期:1994-04-01 00:00:00
abstract::The modulation of GnT-V activity by signaling molecules in PI-3-K/PKB pathway in human hepatocarcinoma cell line 7721 was studied. GnT-V activity was determined after the transfection of sense or antisense cDNA of PKB into the cells, as well as the addition of activators, specific inhibitors, and the antibodies to the...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1007177806496
更新日期:2000-05-01 00:00:00
abstract::Glycation (nonenzymatic glycosylation) in the human lens (cortex and nucleus) in senile (nondiabetic) and diabetic cataracts was studied by measuring the extent of early and late glycation products, the content of free epsilon-amino groups and the formation of disulfide bonds in the soluble lens proteins. There was a ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731255
更新日期:1995-10-01 00:00:00
abstract::Amphipathic sulpholipids have been shown to inhibit pancreatic serine proteases due to their detergent-like properties. To evaluate the structural requirement for this inhibitory activity, we examined the effects of various derivatives of sulphoglycolipids, some of which were prepared by deacylation with sphingolipid ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1010988709764
更新日期:2000-11-01 00:00:00
abstract::Trichomonas vaginalis causes the most common non-viral sexually transmitted infection linked to increased risk of premature birth, cervical cancer and HIV. This study defines molecular domains of the parasite surface glycoconjugate lipophosphoglycan (LPG) with distinct functions in the host immunoinflammatory response...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9157-1
更新日期:2009-01-01 00:00:00
abstract::Previous studies had established an over-expression of 9-O-acetylated sialoglycoproteins (Neu5,9Ac(2)-GPs) on lymphoblasts of childhood acute lymphoblastic leukaemia (ALL). Here, we report the discovery and characterization of sialate-O-acetyltransferase enzyme in ALL-cell lines and lymphoblasts from bone marrow of ch...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9163-3
更新日期:2009-01-01 00:00:00
abstract::Human alpha1,3-fucosyltransferase V and -VI (hFucTV and -VI) each contain four potential N-glycosylation sites (hFucTV: Asn60, Asn105, Asn167 and Asn198 and hFucTVI: Asn46, Asn91, Asn153 and Asn184). Glycosylation of the two N-terminal potential N-glycosylation sites (hFucTV: Asn60, Asn105 and hFucTVI: Asn46 and Asn91...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1010917229243
更新日期:2000-12-01 00:00:00
abstract::In aging and diabetes, glycation of collagen molecules leads to the formation of cross-links that could alter the surface charge on collagen fibrils, and hence affect the properties and correct functioning of a number of tissues. The electron-optical stain phosphotungstic acid (PTA) binds to positively charged amino a...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006928403140
更新日期:1998-08-01 00:00:00