Abstract:
:The advent of kinetically controlled Native Chemical Ligation has permitted more efficient sequential Native Chemical Ligation reactions to take place in one pot where one or more of the peptide fragments contains an N-terminal cysteine residue and a C-terminal thioester. The reactivity of the thioester component can dictate how fragments behave through careful choice of leaving group (alkyl or aryl thiol) and the C-terminal amino acid residue. Although thioester reactivity is exquisitely controlled, reactivity of the N-terminal cysteine residue has been curbed using protecting groups, usually the thiazolidine-4-carboxo (Thz) group as it can be removed in the presence of the thioester at acidic pH. Only recently has the concept of orthogonal ligation been extended to thiol auxiliary mediated Native Chemical Ligation (a.k.a. Extended Ligation) which, owing to their inherent difference in reactivity, have allowed peptides to be selectively extended at the C-terminus without recourse to protecting groups on the N-terminus. Herein we explored the compatibility of acyl transfer auxiliaries with peptide thioester production via an N-->S acyl shift for this purpose.
journal_name
Biopolymersjournal_title
Biopolymersauthors
Ackrill T,Anderson DW,Macmillan Ddoi
10.1002/bip.21473subject
Has Abstractpub_date
2010-01-01 00:00:00pages
495-503issue
4eissn
0006-3525issn
1097-0282journal_volume
94pub_type
杂志文章相关文献
BIOPOLYMERS文献大全abstract::alpha,beta-Dehydro amino acid residues are known to constrain the peptide backbone to the beta-bend conformation. A pentapeptide containing only one alpha,beta-dehydrophenylalanine (delta Phe) residue has been synthesized and crystallized, and its solid state conformation has been determined. The pentapeptide Boc-Leu-...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360350202
更新日期:1995-02-01 00:00:00
abstract::The general properties of hydroxyethylcellulose (HEC) grafted with 3-glycidoxypropyltrimethoxysilane (GPTMS) or 3-glycidoxypropylmethyldiethoxysilane (GPDMS) were studied for potential biomedical applications. The graft involved a Williamson reaction between the free hydroxyl function of HEC and the epoxy function of ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10053
更新日期:2002-04-05 00:00:00
abstract::Individual ethidium-stained DNA molecules, embedded in an agarose gel made with electrophoresis buffer (0.05 molar salt), are observed using a fluorescence microscope. In the first experiment, open circular 66 kilobase pair (kbp) plasmids, immobilized by agarose fibers threaded through their centers, display entropic ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360290807
更新日期:1990-07-01 00:00:00
abstract::Amyloid aggregates have been implicated in the pathogenesis of diseases such as type 2 diabetes, Alzheimer's, Parkinson's, and prion disease. Recently determined microcrystal structures of several short peptide segments derived from fibril-forming proteins revealed coexistence of alternative aggregation modes (amyloid...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21731
更新日期:2012-01-01 00:00:00
abstract::Raman spectra of series of aqueous solutions of peptides containing two amino acids, glycine-X, alanine-X, and serine-X, where X is an uncharged amino acid, show that the amide III band shifts systematically to lower frequencies as the side chain of the X amino acid becomes larger. The range of this shift is about 20 ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360300511
更新日期:1990-01-01 00:00:00
abstract::Different hexameric forms of insulin have been crystallized from a variety of conditions. In the presence of 1% phenol, 1.0 M sodium chloride, and at a pH of 8.5, a rhombohedral form is produced with two monomers in the asymmetric unit, space group R3, a = 79.92 A and c = 40.39 A. The structure has been solved and ref...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360320422
更新日期:1992-04-01 00:00:00
abstract::The conformation of thymosin beta 9 in solution of 40% (v/v) 1,1,1,3,3,3-hexafluoro-2-propanol-d2 in water has been investigated by two-dimensional 1H-nmr spectroscopy. Under this condition thymosin beta 9 adopts an ordered structure. The determination of the conformation of the peptide was based on a set of 304 appro...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/(SICI)1097-0282(199705)41:6<623::AID-BIP3>
更新日期:1997-05-01 00:00:00
abstract::Physiological properties of soluble antigen-antibody (Ag-Ab) complexes depend in part on the size of the complexes. In previous work, the size distribution and structure of model Ag-Ab complexes were determined by electron microscopy. In this study, we used constrained regularization analysis of quasi-elastic light sc...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360311107
更新日期:1991-10-01 00:00:00
abstract::This work concerns the aggregation properties of (Gly-Val-Gly-Val-Pro)(251) rec, a polypentapeptide reflecting a highly conserved repetitive unit of the bioelastomer, elastin. On raising the temperature of aqueous solutions above 25 degrees C, this polypeptide was already known to undergo concurrent conformational cha...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/1097-0282(200107)59:1<51::AID-BIP1005>3.0.
更新日期:2001-07-01 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::A large number of potent and selective therapeutic agents, useful for the treatment of several diseases, have been isolated from natural sources. For example, the most active thrombin inhibitors are those secreted by the salivary glands of leeches. One peculiar feature of these agents is the lack of any significant in...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/(SICI)1097-0282(1999)51:1<19::AID-BIP4>3.0
更新日期:1999-01-01 00:00:00
abstract::Previous studies have demonstrated that His 12 plays a major role in the pH-dependent stability of the helix formed by the isolated C-peptide (residues 1-13 of ribonuclease A). Here, amino acid replacement experiments show that His 12+ stabilizes the C-peptide helix chiefly by interacting with Phe 8. The Phe 8 ... His...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360290104
更新日期:1990-01-01 00:00:00
abstract::The dissociation and assembly of quadruplex DNA structures (and a few quadruplex RNAs) have been characterized at several levels of rigor, ranging from gross descriptions of factors that govern each process, to semiquantitative comparisons of the relative abilities of these factors to induce stabilization or destabili...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/1097-0282(2000/2001)56:3<147::AID-BIP10011
更新日期:2000-01-01 00:00:00
abstract::The structural evolution of regenerated Bombyx mori silk fibroin during shearing with a Couette cell has been studied in situ by synchrotron radiation small- and wide-angle x-ray scattering techniques. An elongation of fibroin molecules was observed with increasing shear rate, followed by an aggregation phase. The agg...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20083
更新日期:2004-07-01 00:00:00
abstract::A Monte Carlo method has been developed for generating the conformations of short single-stranded DNAs from arbitrary starting states. The chain conformers are constructed from energetically favorable arrangements of the constituent mononucleotides. Minimum energy states of individual dinucleotide monophosphate molecu...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360330109
更新日期:1993-01-01 00:00:00
abstract::Synthetic RNA poly[r(A-T)] has been synthesized and its CD spectral properties compared to those of poly[r(A-U)], poly[d(A-T)], and poly[d(A-U)] in various salt and ethanolic solutions. The CD spectra of poly[r(A-T)] in an aqueous buffer and of poly[d(A-T)] in 70.8% v/v ethanol are very similar, suggesting that they b...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.360290210
更新日期:1990-02-05 00:00:00
abstract::The use of peptide carriers, termed "cell-penetrating peptides (CPPs)" has attracted much attention due to their potential for cellular delivery of hydrophilic molecules with pharmacological interest, overcoming the membrane barrier. These peptides are able to deliver attached cargos in a nontoxic manner, with the upt...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21367
更新日期:2010-01-01 00:00:00
abstract::13C and (31)P NMR spectra of a transmembrane peptide, [1-(13)C]Ala(14)-labeled A(6-34), of bacteriorhodopsin incorporated into dimyristoylphosphatidylcholine (DMPC) bilayer were recorded to clarify its dynamics and orientation in the lipid bilayer. This peptide is shown to take an alpha-helical form both in liquid cry...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10021
更新日期:2002-02-01 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::Computer simulations can provide in principle quantitative correlation between the structures of DNA polymerases and the replication fidelity. This paper describes our progress in this direction. Using several theoretical approaches, including the free energy perturbation (FEP), linear response approximation (LRA), an...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10244
更新日期:2003-03-01 00:00:00
abstract::Water-mediated contacts are known as an important recognition tool in trp-repressor operator systems. One of these contacts involves two conserved base pairs (G(6).C(-6) and A(5). T(-5)) and three amino acids (Lys 72, Ile 79, and Ala 80). To investigate the nature of these contacts, we analyzed the X-ray structure (PD...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.20023
更新日期:2004-04-15 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 discovery of the prototype delta opioid antagonists TIPP (H-Tyr-Tic-Phe-Phe-OH) and TIP (H-Tyr-Tic-Phe-OH) in 1992 was followed by extensive structure-activity relationship studies, leading to the development of analogues that are of interest as pharmacological tools or as potential therapeutic agents. Stable TIPP...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/(SICI)1097-0282(1999)51:6<411::AID-BIP4>3.
更新日期:1999-01-01 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::Oxaliplatin (OXA) was coupled to PEGylated polyamidoamine dendrimers of fourth generation (G4-PEG@OXA) in the comparison to PEGylated ones of odd generation (G3.5-PEG@OXA). Proton nuclear magnetic resonance and Fourier-transform infrared spectroscopy were used to confirm the successful incorporation of OXA as well as ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.23272
更新日期:2019-07-01 00:00:00
abstract::The design, synthesis, and evaluation of a novel series of receptors for protein surface recognition are described. The design of these agents is based around the attachment of four constrained peptide loops onto a central calix[4]arene scaffold. This arrangement mimics the role of the hypervariable loops in antibody ...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/(SICI)1097-0282(1998)47:4<285::AID-BIP4>3.
更新日期:1998-01-01 00:00:00
abstract::Our previous studies of the potential utility of the C(alpha)D(alpha) stretch frequency, nu(CD), as a tool for determining conformation in peptide systems (Mirkin and Krimm, J Phys Chem A 2004, 108, 10923-10924; 2007, 111, 5300-5303) dealt with the spectroscopic characteristics of isolated alanine peptides with alpha(...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.21250
更新日期:2009-09-01 00:00:00
abstract::Pig citrate synthase (PCS) can be used as a model enzyme to gain some insight into the structural basis of protein thermostability. The thermal unfolding characteristics of the specific secondary structure elements within PCS were monitored in detail by following changes in its amide I band components. The result of o...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/bip.10392
更新日期:2003-08-01 00:00:00
abstract::Designed ligands that inhibit protein-protein interactions involved in gene expression are valuable as reagents for genomics research and as leads for drug discovery efforts. Selective modulation of protein-protein interactions has proven to be a daunting task for synthetic ligands; however, the last decade has seen s...
journal_title:Biopolymers
pub_type: 杂志文章,评审
doi:10.1002/bip.21546
更新日期:2011-01-01 00:00:00
abstract::A theoretical study is presented of the influence of salt bridges between cationic side chains and DNA phosphates on DNA conformation and flexibility. The DNA sequence studied is that of the catabolite activator protein binding oligomer from the crystallized complex. The effect of salt bridges is modeled by neutraliza...
journal_title:Biopolymers
pub_type: 杂志文章
doi:10.1002/(SICI)1097-0282(19990405)49:4<313::AID-BIP
更新日期:1999-04-01 00:00:00