Abstract:
:The comprehensive structural analysis reported herein of eight N-glycopeptides, in three different solvents, is based on quantitative CD experiments, homonuclear nuclear Overhauser effect measurements, and molecular dynamics (MD) calculations. Although several orientations of the two amide planes attached to the carbohydrate pyranose ring are possible, according to NOE, CD data, and MD simulations, of all of the glycopeptide models, regardless of the type of the carrier peptide, only one dominant conformer population was found. This conformer is characterized by a nearly trans orientation of the CH and NH hydrogens of both acetamido groups. This finding is in perfect agreement with x-ray crystallographic data on the solid state conformation of the 1-N-acetyl- and 1-N-(beta-aspartyl)-2-acetamido-2-deoxy-beta-D-glucopyranosyla min e. The precise identification of this dominant conformer of N-glycopeptides in solution was the major question addressed herein by the structural analyses. A "CD additivity" experiment was carried out using an equimolar solution of Boc-Pro-Asp-NHCH3 and 1-N-acetyl-3,4,6- tri-O-acetyl-2-acetamido-2-deoxy-beta-D-glucopyranosylamine at ambient temperature in acetonitrile. The CD spectrum obtained from the equimolar solution of the above two molecules (the "spectroscopic sum") was identical with the CD curve obtained from the algebraic summation of the individually recorded CD spectra of the peptide and the carbohydrate moiety ("mathematical sum"). The global picture of the CD spectral analyses of the eight parent peptides with the eight N-glycopeptides revealed that in trifluoroethanol and acetonitrile, the side-chain modification of the Asn models (natural N-glycopeptide analogues) by N-glycosylation has a significant effect on the conformation of the carrier peptide, resulting in a decrease in the original type I beta-turn content. Simultaneously, the type II beta-turn conformational percentage increased to approximately 20%. Such a conformational ratio change seems to be larger than the expected errors arising from the CD analyses, and agrees with the results of MD calculations. N-glycosylation of Asn residues causes perturbations, not only through the covalent bond, but also through specific hydrogen bonds between the backbone and side chain atoms. CD spectroscopy, augmented by efficient CD curve deconvolution techniques, has proved to be a useful tool for studying multicomponent conformer mixtures of small linear peptides in solution and changes of conformational equilibria caused by N-glycosylation.
journal_name
Biopolymersjournal_title
Biopolymersauthors
Perczel A,Kollát E,Hollósi M,Fasman GDdoi
10.1002/bip.360330416subject
Has Abstractpub_date
1993-04-01 00:00:00pages
665-85issue
4eissn
0006-3525issn
1097-0282journal_volume
33pub_type
杂志文章相关文献
BIOPOLYMERS文献大全abstract::The enhanced nucleophilicity and redox sensitivity of the thiol group renders cysteine residues susceptible to numerous electrophilic and oxidative post-translational modifications to form disulfides, sulfenic acids, nitrosothiols, and lipid-modified species. Outside of these well-characterized modifications of cystei...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/bip.22252
更新日期:2014-02-01 00:00:00
abstract::The x-ray conformations of 5-, 7-, 9-, and 12-residue loops in bovine pancreatic trypsin inhibitor (BPTI) were predicted by the use of multiple independent Monte Carlo simulating annealing (MCSA) runs starting from random conformations. Four buried water molecules interacted with a 12-residue loop that started at resi...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/1097-0282(20010405)58:4<359::AID-BIP1013>3
更新日期:2001-04-05 00:00:00
abstract::Peptoids, oligomers of N-substituted glycine, have been valuable targets for study and diverse application as peptidomimetics and as nanomaterials. Their conformational heterogeneity has made the study of peptoid structures using high-resolution analyses challenging, limiting our understanding of the physiochemical fe...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21605
更新日期:2011-01-01 00:00:00
abstract::The applicability of the FTIR attenuated total reflectance technique for in situ monitoring of plant physiological processes such as leaf senescence and aging has been examined. Difference spectra obtained by subtracting the spectrum of the young plant leaf from that of the older one revealed positive bands at 1650-15...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10297
更新日期:2003-01-01 00:00:00
abstract::The periodical D-band pattern is generally considered a unique ultrastructural feature shared by all fibril-forming collagens, which correlates with the intrafibril, paracrystalline array of tropocollagen monomers. Distinct band patterns have been reported, however, for collagen stained long-spacing (SLS) crystallites...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/1097-0282(200011)54:6<448::AID-BIP80>3.0.C
更新日期:2000-11-01 00:00:00
abstract::Flow linear dichroism measurements extended into the vacuum uv region yield inclinations for the base normal from the helix axis of 21 degrees for dA and 40 degrees for dT in the X-form of poly(dAdT).poly(dAdT). These inclination angles are similar to the B form of the synthetic polymer, but the axes around which the ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360341104
更新日期:1994-11-01 00:00:00
abstract::DMT1, also known as Nramp2, is an iron transporter, and belongs to the family of Nramp proteins. Disease-causing mutations both in Nramp1 and Nramp2 occurring at the conserved two adjacent glycine residues located within the fourth transmembrane domain (TM4) suggest that TM4 may serve an important biological function....
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20204
更新日期:2005-03-01 00:00:00
abstract::Software to automate the process of extracting molecular interactions from three-dimensional (3D) structures has been developed that records these as Biomolecular Interaction Network Database (BIND) pairwise interaction records. Full annotation of BIND records is provided through a database processing tool called MMDB...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/1097-0282(2001/2002)61:2<111::AID-BIP10143
更新日期:2001-01-01 00:00:00
abstract::Spiders can produce up to seven different types of silks or glues with different mechanical properties. Of these, flagelliform (Flag) silk is the most elastic, and aciniform (AcSp1) silk is the toughest. To produce a chimeric spider silk (spidroin) FlagR -AcSp1R , we fused one repetitive module of flagelliform silk fr...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.23404
更新日期:2020-12-01 00:00:00
abstract::Elucidation of mechanisms underlying collagen fibril assembly and matrix-induced guidance of cell fate will contribute to the design and expanded use of this biopolymer for research and clinical applications. Here, we define how Type I collagen oligomers affect in-vitro polymerization kinetics as well as fibril micros...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21537
更新日期:2011-02-01 00:00:00
abstract::The conformational study on Arg-Gly-Asp (RGD)-containing tetrapeptides in the unhydrated and hydrated states has been carried out using the force field ECEPP/3 and the hydration shell model. The tetrapeptides studied here are H-RGDX-OH (X = Trp, Tyr, Phe, Leu, Val, Cys, Gln, and Ser), which show the inhibitory activit...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10067
更新日期:2002-04-15 00:00:00
abstract::To validate the existing hypothesis put forward by Navarro et al., we performed single crystal X-ray diffraction structural analysis of a designed model peptide incorporating an unsubstituted achiral γ-aminobutyric acid: Boc-Pro-γ-Abu-OH (1) lacking C-terminal amide group. The analysis established existence of an over...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21511
更新日期:2010-11-01 00:00:00
abstract::The sweet protein brazzein isolated from the fruit of the African plant, Pentadiplandra brazzeana Baillon is 2000-500 times sweeter than sucrose and consists of 54 amino acid residues with four intramolecular disulfide bonds. Brazzein was prepared by the fluoren-9-yl-methoxycarbonyl solid-phase method, and was identic...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/(sici)1097-0282(199607)39:1<95::aid-bip10>
更新日期:1996-07-01 00:00:00
abstract::MUC1 mucin is a large transmembrane glycoprotein whose extracelluler domain is composed of repeating units of a 20 amino acid sequence. In the cancer associated state, this protein expression becomes upregulated and underglycosylated. Previous studies, which show an enhanced binding of a 5-repeat over a 1-repeat MUC1 ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20190
更新日期:2005-02-05 00:00:00
abstract::Peptide-polysaccharide matrices can mimic extracellular matrix structure and function and are useful for tissue and cell engineering. The spacer between the peptide and the polysaccharide is important for both peptide conformation and the interaction between the peptide and receptors. Here, the effect of a spacer on t...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22785
更新日期:2016-11-04 00:00:00
abstract::A new family of small plant peptides was recently described and found to be widespread throughout the Millereae and Heliantheae tribes of the sunflower family Asteraceae. These peptides originate from the post-translational processing of unusual seed-storage albumin genes, and have been termed PawS-derived peptides (P...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22901
更新日期:2016-11-01 00:00:00
abstract::Near uv CD spectra of Trp residues in proteins frequently show a complex line shape deriving from the overlap of 1La and 1Lb electronic transitions. This study presents an original empirical method of resolving these components, based on the near uv CD spectra of well-defined complexes of calmodulin domains with targe...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/(SICI)1097-0282(199806)45:7<493::AID-BIP3>
更新日期:1998-06-01 00:00:00
abstract::Ribonuclease A is the archetype of a functionally diverse superfamily of vertebrate-specific ribonucleases. Inhibitors of its action have potential use in the elucidation of the in vivo roles of these enzymes and in the treatment of pathologies associated therewith. Derivatives of adenosine 5'-pyrophosphate are the mo...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21158
更新日期:2009-12-01 00:00:00
abstract::The X-ray diffraction analysis of a stereocontrolled heterochiral designed model peptide Boc-(D) Pro-Thr-OMe (1) revealed the existence of an unusual folded molecular structure, stabilized via an effective unconventional C---H…O type intramolecular hydrogen-bond, encompassing a noncovalent 12-membered ring-motif. Toge...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21705
更新日期:2012-01-01 00:00:00
abstract::H-Pro-Pro-Asp-NH2 is a highly active and selective catalyst for asymmetric aldol reactions. Here, the versatility of H-Pro-Pro-Asp-NH2 has been further improved by immobilization on a solid support and functionalization with a short polyethylene glycol linker at the C-terminus. The development, synthesis, and the cata...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20393
更新日期:2006-01-01 00:00:00
abstract::Despite the positive results observed in vitro and in vivo, clinical trials with bioactive peptides are generally hampered by their fast degradation in the biological system. Two bioactive peptides, P20 (CSSRTMHHC) and the combined peptide C (CVNHPAFACGYGHTMYYHHYQHHL) have been identified as anticancer therapeutics. C...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.23029
更新日期:2017-09-01 00:00:00
abstract::We have determined using NMR the structure of the complex between the third double-stranded RNA-binding domain (dsRBD3) of Drosophila Staufen protein and a RNA stem-loop with optimal binding properties in vitro. This work was designed to understand how dsRBD proteins bind RNA and to investigate the role of Staufen dsR...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/1097-0282(1999)52:4<181::AID-BIP1003>3.0.C
更新日期:1999-01-01 00:00:00
abstract::The differences in the absorbance in the mid infrared region (Mid IR) between normal and abnormal tissues have been shown to be a possible criterion for the detection of different forms of cancer. The present work aimed to study the effects of cell growth and DNA synthesis on the RNA/DNA ratio, which is a promising pa...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21048
更新日期:2008-11-01 00:00:00
abstract::Constrained azapeptides were designed based on the Ala-Val-Pro-Ile sequence from the second mitochondria-derived activator of caspases (Smac) protein and tested for ability to induce apoptosis in cancer cells. Diels-Alder cyclizations and Alder-ene reactions on azopeptides enabled construction of a set of constrained ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22851
更新日期:2016-05-01 00:00:00
abstract::We have previously described [K. M. Sullivan and D. M. J. Lilley (1986) Cell 47, 817-827] a set of sequences, called C-type inducing sequences, which cause cruciform extrusion by adjacent inverted repeats to occur by an abnormal kinetic pathway involving a large denatured region of DNA. In this paper we apply statisti...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360280810
更新日期:1989-08-01 00:00:00
abstract::Cyclotides are multifunctional plant cyclic peptides containing 28-37 amino acid residues and a pattern of three disulfide bridges, forming a motif known as the cyclic cystine knot. Due to their high biotechnological potential, the sequencing and characterization of cyclotide genes are crucial not only for cloning and...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22938
更新日期:2016-11-01 00:00:00
abstract::With the availability of accurate methods to treat the electrostatic long-range interactions, molecular dynamics simulations have resulted in refined dynamical models of the structure of the hydration shell around RNA motifs. The models reviewed here range from basic Watson-Crick to more specific noncanonical base pai...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/1097-0282(2000)56:4<266::AID-BIP10027>3.0.
更新日期:2000-01-01 00:00:00
abstract::In a seminal paper, Pakula and Sauer (Nature, 1990, 344, 363-364) demonstrated that the increase in side-chain hydrophobicity has a reverse relationship with protein stability. We have addressed this problem with several examples of mutants that span at different locations in protein structure based on secondary struc...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21187
更新日期:2009-07-01 00:00:00
abstract::Recombinant murine amelogenins M179 and M166 were expressed in Escherichia coli and purified. The aggregation properties of these amelogenins have been investigated in aqueous solutions as well as acetonitrile-containing solutions using dynamic light scattering. Dynamic light scattering provides direct measurement of ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360341006
更新日期:1994-10-01 00:00:00
abstract::Partially acetylated, high molecular weight glucuronans were produced by a Sinorhizobium meliloti mutant strain. Two native glucuronan samples with various degrees of acetylation were sonicated to obtain lower molecular weight samples and with low viscosity suitable for chemical modification and (13)C NMR experiments....
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10134
更新日期:2002-06-01 00:00:00