Abstract:
:A series of cyclic retro-inverso dipeptides--2-[(4-hydroxy)benzyl]-5-benzyl-4,6(1H,2H,3H,5H)-pyrimidinedi one (c[mPhe-gTyr]), 2-benzyl-5-[(4-hydroxy)benzyl]-4,6(1H,2H,3H,5H)-pyrimidinedione (c[mTyr-gPhe]), and 2-benzyl-5-amino-5-[(4-hydroxy)benzyl]-4,6(1H,2H,3H,5H)-pyrimidinedione (c[(alpha-amino)mTyr-gPhe])--were synthesized in order to define the minimum structural requirements for binding affinity with opiate receptors and biological activity. Although the first two compounds lack a free amine proposed to be necessary for receptor recognition, the c[mPhe-gTyr] and c[mTyr-gPhe] analogues serve as model molecules in conformational studies of the target analogue, c[(alpha-amino)mTyr-gPhe]. The cis- and trans-c[(alpha-amino)mTyr-gPhe] contain all the functional groups such as the amine and phenolic groups in the tyrosine, and the aromatic group in the phenylalanine, necessary for opiate activity. In addition, the c[(alpha-amino)mTyr-gPhe] analogues possess similar geometries to the Tyr-Pro part of morphiceptin (Tyr-Pro-Phe-Pro-NH2) whose high mu-receptor activity is attributed to conformations with the Tyr-Pro amide bond in a cis conformation because the peptide bonds assume a cis conformation. However, both analogues are inactive in the guinea pig ileum and the mouse vas deferens assays. This may result from wrong orientation of the benzyl group of the gPhe residue with respect to the (alpha-amino)mTyr residue. Conformational studies of these molecules using 1H-nmr spectroscopy and molecular mechanics calculations will be reported in the following paper. Results of conformational analysis should provide information about backbone-side-chain interactions in the retro-inverso peptide chains since all the fundamental structural elements of the retro-inverso peptides are included in these model systems even though the peptide bonds must assume a cis conformation.
journal_name
Biopolymersjournal_title
Biopolymersauthors
Nunami K,Yamazaki T,Goodman Mdoi
10.1002/bip.360311307subject
Has Abstractpub_date
1991-11-01 00:00:00pages
1503-12issue
13eissn
0006-3525issn
1097-0282journal_volume
31pub_type
杂志文章相关文献
BIOPOLYMERS文献大全abstract::Human saliva contains hundreds of small proline-rich peptides originated by the proteolytic cleavage of the salivary basic Proline-Rich Proteins. Nevertheless only for few of them a specific biological activity has been assigned to date. Among them, the 1932 Da peptide (p1932) has been patented as an anti-HIV agent. I...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22889
更新日期:2016-09-01 00:00:00
abstract::Recent results from molecular dynamics (MD) simulations on hydration of DNA with respect to conformation are reviewed and compared with experimental data. MD simulations of explicit solvent around DNA can now give a detailed model of DNA that not only matches well with the experimental data but provides additional ins...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/(SICI)1097-0282(1998)48:4<199::AID-BIP2>3.
更新日期:1998-01-01 00:00:00
abstract::The structure of starch was studied using small-angle x-ray scattering (SAXS). The scattering data was modeled by considering a finite stack of alternating lamellae that are allowed to fluctuate both along the layer repeat direction and along the transverse layer direction. Analysis in this way of the SAXS data from s...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10341
更新日期:2003-06-01 00:00:00
abstract::A model of protein-chaperone interaction as a two-phase (unfolding/refolding) iterative annealing mechanism able to promote structural segregation of hydrophobic and hydrophilic monomers and thereby facilitate access to nativelike states has recently been applied successfully to two 22-mers of the Honeycutt and Thirum...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10148
更新日期:2002-07-15 00:00:00
abstract::TC5b is a 20 residue polypeptide notable for its compact tertiary structure, a rarity for a short peptide. This structure is due to the "Trp-cage" motif, an association of aromatic, Pro, and Gly residues. The structure of TC5b has been fully characterized by NMR and electronic circular dichroism (ECD) studies, but has...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20709
更新日期:2007-01-01 00:00:00
abstract::The transient electric birefringence of two small DNA restriction fragments of the same molecular weight, one of which migrates anomalously slowly on polyacrylamide gels, has been investigated. Both fragments exhibit negative birefringence. The decay of the birefringence of the anomalously slowly migrating fragment is...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360311318
更新日期:1991-11-01 00:00:00
abstract::The total synthesis of a peptide segment corresponding to the DNA-binding segment of Sp1 (positions 532-623) using a native chemical ligation approach is described. The folding of the synthetic segment in the presence of Zn(II) gave a zinc-coordinated protein. The dissociation constant (K(D)) for the DNA binding of th...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10562
更新日期:2004-01-01 00:00:00
abstract::Collagen is a natural protein, which is used as a vital biomaterial in tissue engineering. The major concern about native collagen is lack of its thermal stability and weak resistance to proteolytic degradation. In this scenario, the crosslinking compounds used for stabilization of collagen are mostly of chemical natu...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22473
更新日期:2014-08-01 00:00:00
abstract::The question of long-range allosteric transitions of DNA secondary structure and their possible involvement in transcriptional activation is discussed in the light of new results. A variety of recent evidence strongly supports a fluctuating long-range description of DNA secondary structure. Balanced equilibria between...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/(SICI)1097-0282(1997)44:3<283::AID-BIP7>3.
更新日期:1997-01-01 00:00:00
abstract::Cytochrome c3 from Desulfovibrio gigas is electrostatically adsorbed on Ag electrodes coated with self-assembled monolayers (SAMs) of 11-mercaptoundecanoic acid. The redox equilibria and electron transfer dynamics of the adsorbed four-heme protein are studied by surface enhanced resonance Raman spectroscopy. Immobiliz...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10101
更新日期:2002-01-01 00:00:00
abstract::CD and nmr spectroscopy were used to compare the conformational properties of two related peptides. One of the peptides, Model AB, was designed to adopt a helix-turn-extended strand (alpha beta) tertiary structure in water that might be stabilized by hydrophobic interactions between two leucine residues in the amino-t...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360360202
更新日期:1995-08-01 00:00:00
abstract::Circular dichroism using synchrotron radiation (SRCD) can extend the spectral range down to approximately 130 nm for dry proteins, potentially providing new structural information. Using a selection of dried model proteins, including alpha-helical, beta-sheet, and mixed-structure proteins, we observe a low-wavelength ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21011
更新日期:2008-09-01 00:00:00
abstract::We report on the conformation of a tetrasaccharide fragment in the repeating subunit of the cell wall polysaccharide of Streptococcus mitis J22, a receptor for the lectin of Actinomyces viscosus T14V in a bacterial coaggregation that is important in the ecological interactions of oral bacteria. Although there is consi...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/(SICI)1097-0282(199603)38:3%3C339::AID-BIP
更新日期:1996-03-01 00:00:00
abstract::Interactions between biological macromolecules have characteristic values of affinity and specificity that are set according to the biological function that is served by the interaction in the organism. Here we examine the molecular mechanisms that are used to achieve the required values of affinity and specificity in...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/(SICI)1097-0282(1997)44:2<181::AID-BIP5>3.
更新日期:1997-01-01 00:00:00
abstract::The title compound represents the smallest member of cyclic proline peptides corresponding to the general formula c(DDLL-Pro4)n with a strictly D,D,L,L double-alternating sequence of the chiral amino acid residues. The cyclopeptides with n greater than or equal to 2 could be synthesized from both DDLL-Pro4 (1) and DLL...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360310618
更新日期:1991-05-01 00:00:00
abstract::Experimental and computational methods of infrared microspectroscopy (IRI-MSP) and infrared spectral mapping (ISM) are presented. These methods are subsequently applied to the analysis of cirrhotic liver tissue. The sensitivity of infrared spectral mapping toward spectral changes caused by disease will be demonstrated...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/1097-0282(2000)57:5<282::AID-BIP50>3.0.CO;
更新日期:2000-01-01 00:00:00
abstract::Among the most exciting functional features of G-protein coupled receptors (GPCRs) that are coming into focus lately are those relating to the role and structural characteristics of their oligomerization (mostly homo- and heterodimers). The structural underpinnings of these novel functional insights are still not clea...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10311
更新日期:2002-01-01 00:00:00
abstract::Prolonged exposure (>90 days) of bovine beta-lactoglobulin (BLG) to subdenaturing concentrations of either urea or potassium thiocyanate resulted in the formation of ordered polymers in the form of fibrils. The fibrils obtained with each chaotrope showed major differences in morphology, surface properties, thiol acces...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20704
更新日期:2007-05-01 00:00:00
abstract::Using a variety of spectroscopic techniques, a number of molecular functionalities have been studied in relation to the adsorption process of proteins to air-water interfaces. While ellipsometry and drop tensiometry are used to derive information on adsorbed amount and exerted surface pressure, external reflection cir...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20036
更新日期:2004-05-01 00:00:00
abstract::Structural data produced by a 2-ns molecular dynamics (MD) simulation on Geobacillus alanine racemase (AlaR; PDB: 1SFT) was used to study hydration around the two AlaR active sites. AlaR is a crucial enzyme for bacterial cell wall biosynthesis. It has been shown previously that the potency of an inhibitor can be incre...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20893
更新日期:2008-03-01 00:00:00
abstract::Cyclic tri-β-peptide having tetrathiafulvalene (TTF) at the side chain was synthesized to prepare a peptide nanotube aligning TTF side chains along the nanotube. The polarized light microscopic observations revealed crystallization of the cyclic peptide by the vapor diffusion method. Fourier-transform infrared and ele...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22850
更新日期:2016-05-01 00:00:00
abstract::We describe a method to determine the magnitude of protein-induced DNA bends relative to a set of standard A tract bends using comparative gel electrophoresis. The DNA bend of interest was that induced by the catabolite activator protein (CAP), the transcriptional activator protein of the lac operon. The set of compar...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360290106
更新日期:1990-01-01 00:00:00
abstract::Calculations of the normal mode spectrum of a netropsin-DNA complex, an isolated DNA helix of the same sequence, and a free netropsin molecule were carried out and compared with observations. We find that the frequency of modes of the complex that are primarily vibrations localized to the helix are relatively unchange...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360350611
更新日期:1995-06-01 00:00:00
abstract::The abnormal aggregation of amyloid proteins is reported to play a critical role in the etiology of neurodegenerative disorders. Studies have shown that excessive ferric irons are associated with the misfolding of amyloid proteins, and that (-)-epigallocatechin gallate (EGCG) is a good metallic ion chelator with inhib...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22752
更新日期:2016-02-01 00:00:00
abstract::Additive physical properties of DNA double strand polymers have been expanded in terms of 8 irreducible parameters. This provided consistency relations among the corresponding 10 duplex dimer contributions. To allow for oligomer analysis, end parameters were often added, and this would add extra degrees of freedom to ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.22214
更新日期:2013-08-01 00:00:00
abstract::The self-cleaving hepatitis delta virus (HDV) ribozyme is essential for the replication of HDV, a liver disease causing pathogen in humans. The catalytically critical nucleotide C75 of the ribozyme is buttressed by a trefoil turn pivoting around an extruded G76. In all available crystal structures, the conformation of...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20693
更新日期:2007-04-05 00:00:00
abstract::A de novo polypeptide GH(6)[(GA)(3)GY(GA)(3)GE](8)GAH(6) (YE8) was designed and genetically engineered to form antiparallel beta-strands of GAGAGA repeats. Modulation of pH enables control of solubility, folding, and aggregation of YE8 by control of the overall polypeptide charge, a consequence of the protonation or d...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20730
更新日期:2007-07-01 00:00:00
abstract::The oxidation of methionine to methionine sulfoxide both in vivo and in vitro can lead to the loss of biological activity in a variety of proteins. This loss of activity can be reversed by an enzyme called methionine sulfoxide reductase. The gene for this enzyme has been cloned and sequenced from a variety of prokaryo...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/1097-0282(2000)55:4<288::AID-BIP1002>3.0.C
更新日期:2000-01-01 00:00:00
abstract::Proteases play crucial roles in various biological processes, and their activities are essential for all living organisms-from viruses to humans. Since their functions are closely associated with many pathogenic mechanisms, their inhibitors or activators are important molecular targets for developing treatments for va...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/bip.22780
更新日期:2016-11-04 00:00:00
abstract::Relevant parameters and stereochemical consequences of helices [alpha-helix, 3(10)-helix, beta-bend ribbon spiral, gamma-helix, 2.0(5)-helix, poly(Pro)(n) type-I and -II helices, and collagen triple helix] of peptides based on alpha-amino acids for use as templates in various branches of chemistry are briefly discusse...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/bip.20357
更新日期:2006-01-01 00:00:00