On-resin N-terminal peptoid degradation: Toward mild sequencing conditions.

Abstract:

:A novel approach to sequentially degrade peptoid N-terminal N-(substituted)glycine residues on the solid-phase using very mild conditions is reported. This method relies on the treatment of resin-bound, bromoacetylated peptoids with silver perchlorate in THF, leading to an intramolecular cyclization reaction to liberate the terminal residue as a N-substituted morpholine-2,5-dione, resulting in a truncated peptoid upon hydrolysis and a silver bromide byproduct. Side-chain functional group tolerance is explored and reaction kinetics are determined. In a series of pentapeptoids possessing variable, non-nucleophilic side-chains at the second position (R(2) ), we demonstrate that sequential N-terminal degradation of the first two residues proceeds in 87% and 74% conversions on average, respectively. We further demonstrate that the degradation reaction is selective for peptoids, and represents substantial progress toward a mild, iterative sequencing method for peptoid oligomers. © 2016 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 726-736, 2016.

journal_name

Biopolymers

journal_title

Biopolymers

authors

Proulx C,Noë F,Yoo S,Connolly MD,Zuckermann RN

doi

10.1002/bip.22884

subject

Has Abstract

pub_date

2016-09-01 00:00:00

pages

726-36

issue

5

eissn

0006-3525

issn

1097-0282

journal_volume

106

pub_type

杂志文章
  • Vibrational CD studies of interchain hydrogen-bonded tripodal peptides.

    abstract::The solution conformations of three trispeptides--L,L,L-1,3,5-C6H3[CH2NHCOCH(X)-NHBoc++ +]3, X = CH3 (Ala) or CH2CH(CH3)2 (Leu), and L,L,L-N(CH2CH2NHCOCH[CH2-CH(CH3)2]NHBoc)3--have been determined from their ir and vibrational CD (VCD) spectra in the NH stretching and carbonyl stretching regions in apolar solution. Th...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360320706

    authors: Paterlini MG,Freedman TB,Nafie LA,Tor Y,Shanzer A

    更新日期:1992-07-01 00:00:00

  • Interaction of processes on different length scales in a bioelastomer capable of performing energy conversion.

    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.

    authors: Manno M,Emanuele A,Martorana V,San Biagio PL,Bulone D,Palma-Vittorelli MB,McPherson DT,Xu J,Parker TM,Urry DW

    更新日期:2001-07-01 00:00:00

  • Identification and characterization of multifunctional cationic and amphipathic peptides from soybean proteins.

    abstract::In this study, we identified and chemically synthesized three cationic and amphipathic peptides (Glycinin-17, BCAS-16, and BCBS-11) from soybean proteins. These peptides had high isoelectric points, high positive net charges, and included multiple hydrophobic amino acids. Subsequently, we identified multiple functions...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.23023

    authors: Taniguchi M,Saito K,Nomoto T,Namae T,Ochiai A,Saitoh E,Tanaka T

    更新日期:2017-07-01 00:00:00

  • Development of a model for the delta-opioid receptor pharmacophore. 4. Residue 3 dehydrophenylalanine analogues of Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) confirm required gauche orientation of aromatic side chain.

    abstract::We have previously proposed a model for the delta-opioid receptor binding conformation of the high affinity tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) based on experimental and theoretical conformational analysis of this peptide and a correlation of conformational preferences of further conformationally restricted...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(sici)1097-0282(199609)39:3<287::aid-bip2>

    authors: Mosberg HI,Dua RK,Pogozheva ID,Lomize AL

    更新日期:1996-09-01 00:00:00

  • Expression and biophysical analysis of a triple-transmembrane domain-containing fragment from a yeast G protein-coupled receptor.

    abstract::Structural characterization of G protein-coupled receptors (GPCRs) is hindered by the inherent hydrophobicity, flexibility, and large size of these signaling proteins. Insights into conformational preferences and the three-dimensional (3D) structure of domains of these receptors can be obtained using polypeptide fragm...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21614

    authors: Caroccia KE,Estephan R,Cohen LS,Arshava B,Hauser M,Zerbe O,Becker JM,Naider F

    更新日期:2011-01-01 00:00:00

  • Conformational preferences and synthesis of isomers Z and E of oxazole-dehydrophenylalanine.

    abstract::Dehydrophenylalanine, ΔPhe, is the most commonly studied α,β-dehydroamino acid. In nature, further modifications of the α,β-dehydroamino acids were found, for example, replacement of the C-terminal amide group by oxazole ring. The conformational properties of oxazole-dehydrophenylalanine residue (ΔPhe-Ozl), both isome...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22852

    authors: Staś M,Bujak M,Broda MA,Siodłak D

    更新日期:2016-05-01 00:00:00

  • Pressure stability of the alpha-helix structure in a de novo designed protein (alpha-l-alpha)(2) studied by FTIR spectroscopy.

    abstract::The pressure-induced structural changes of a de novo designed four-helix bundle protein, (alpha-l-alpha)(2), in aqueous solution have been investigated by FTIR spectroscopy. Changes in the amide I' band intensity show that pressure induces disruption of tertiary interactions and stabilizes the solvated alpha-helical f...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20628

    authors: Takekiyo T,Takeda N,Isogai Y,Kato M,Taniguchi Y

    更新日期:2007-02-05 00:00:00

  • FTIR study on heat-induced and pressure-assisted cold-induced changes in structure of bovine alpha-lactalbumin: stabilizing role of calcium ion.

    abstract::The second derivative FTIR study of heat-induced and pressure-assisted cold-induced changes in the secondary structure of bovine alpha-lactalbumin was carried out for native holoprotein and calcium ion depleted apoprotein. The secondary structure and compactness of alpha-lactalbumin were examined in a temperature rang...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(2001)62:1<29::AID-BIP50>3.0.CO;2

    authors: Dzwolak W,Kato M,Shimizu A,Taniguchi Y

    更新日期:2001-01-01 00:00:00

  • Precise bacterial polyprenol length control fails in Saccharomyces cerevisiae.

    abstract::A comparison of amino acid sequences of yeast Rer2p and Srt1p Z-prenyltransferases shows that the spatial organization of their substrate tunnels agrees with that determined by X-ray for the E. coli undecaprenyl diphosphate synthase (UPPs). The observed trend in the maxima of product length distribution shifted from C...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20715

    authors: Poznański J,Szkopinska A

    更新日期:2007-06-05 00:00:00

  • Use of surface enhanced infrared absorption spectroscopy (SEIRA) to probe the functionality of a protein monolayer.

    abstract::We present a novel infrared method to investigate the functionality of a protein monolayer tethered to a metal substrate. The approach employs Surface Enhanced Infrared Absorption Spectroscopy (SEIRAS), which renders high surface sensitivity by enhancing the signal of the adsorbed protein by up to approximately 2 orde...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20501

    authors: Ataka K,Heberle J

    更新日期:2006-07-01 00:00:00

  • Investigation of stretching vibrations of glycosidic linkages in disaccharides and polysaccharides with use of IR spectra deconvolution.

    abstract::The results are presented for the deconvolution of IR spectra of disaccharides and polysaccharides with alpha and beta configurations of the 1 --> 4 glycosidic linkage (maltose, cellobiose, amylose, and cellulose), as well as of their corresponding monosaccharides (alpha- and beta-D-glucose) in the 1200-920 cm(-1) fre...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(2000)57:4<257::AID-BIP7>3.0.CO;2

    authors: Nikonenko NA,Buslov DK,Sushko NI,Zhbankov RG

    更新日期:2000-01-01 00:00:00

  • Flow linear dichroism and Fourier transform IR spectra reveal geometry for X-form DNA.

    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

    authors: Riazance-Lawrence JH,Kang H,Chou PJ,Johnson WC Jr,Vorlícková M

    更新日期:1994-11-01 00:00:00

  • Cloning and characterization of novel cyclotides genes from South American plants.

    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

    authors: Cunha NB,Barbosa AE,de Almeida RG,Porto WF,Maximiano MR,Álvares LC,Munhoz CB,Eugênio CU,Viana AA,Franco OL,Dias SC

    更新日期:2016-11-01 00:00:00

  • Estimation of strength in different extra Watson-Crick hydrogen bonds in DNA double helices through quantum chemical studies.

    abstract::It was shown earlier, from database analysis, model building studies, and molecular dynamics simulations that formation of cross-strand bifurcated or Extra Watson-Crick hydrogen (EWC) bonds between successive base pairs may lead to extra rigidity to DNA double helices of certain sequences. The strengths of these hydro...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20542

    authors: Bandyopadhyay D,Bhattacharyya D

    更新日期:2006-10-15 00:00:00

  • Structural insight into the XTACC3/XMAP215 interaction from CD and NMR studies on model peptides.

    abstract::TACC3 is a centrosomal adaptor protein that plays important roles during mitotic spindle assembly. It interacts with chTOG/XMAP215, which catalyzes the addition of tubulin dimers during microtubule growth. A 3D coiled-coil model for this interaction is available but the structural details are not well described. To ch...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.23039

    authors: Partida-Hanon A,Treviño MA,Mompeán M,Jiménez MÁ,Bruix M

    更新日期:2017-11-01 00:00:00

  • Correct interpretation of heme protein spectra allows distinguishing between the heme and the protein dynamics.

    abstract::It is shown by using the vibronic approach that the iron displacement out of the porphyrin plane in deoxyheme proteins intermixes the porphyrin pi and axial iron-histidine sigma electronic subsystems. This intermixing explains the substantial coupling of the iron-histidine vibration to the heme Soret excitation, the a...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20039

    authors: Stavrov SS

    更新日期:2004-05-01 00:00:00

  • Single molecule studies of molecular diffusion in cellular membranes: determining membrane structure.

    abstract::Since the advent of single particle/molecule microscopies, researchers have applied these techniques to understanding the fluid membranes of cells. By observing diffusion of membrane proteins and lipids in live cell membranes of eukaryotic cells, it has been found that membranes contain a mosaic of fluid compartments....

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/bip.20801

    authors: Ritchie K,Spector J

    更新日期:2007-10-05 00:00:00

  • Analysis of a new crystal form of procarboxypeptidase B: further insights into the catalytic mechanism.

    abstract::A new triclinic crystal structure form of porcine pancreatic procarboxypeptidase B (PCPB) was obtained at higher resolution than the previously known tetragonal crystal structure. This new crystal polymorph has allowed for a corrected, accurate assignment of residues along the polypeptide chain based on the currently ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21320

    authors: Fernández D,Boix E,Pallarès I,Avilés FX,Vendrell J

    更新日期:2010-02-01 00:00:00

  • Equilibrium unfolding of the poly(glutamic acid)20 helix.

    abstract::The equilibrium structural ensemble of a 20-residue polyglutamic acid peptide (E(20)) was studied with FRET, circular dichroism, and molecular dynamics (MD) simulations. A FRET donor, o-aminobenzamide, and acceptor, 3-nitrotyrosine, were introduced at the N- and C-termini, respectively. Circular dichroism, steady stat...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20719

    authors: Finke JM,Jennings PA,Lee JC,Onuchic JN,Winkler JR

    更新日期:2007-06-15 00:00:00

  • Protein adsorption at air-water interfaces: a combination of details.

    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

    authors: de Jongh HH,Kosters HA,Kudryashova E,Meinders MB,Trofimova D,Wierenga PA

    更新日期:2004-05-01 00:00:00

  • Molecular dynamics simulations of a winter flounder "antifreeze" polypeptide in aqueous solution.

    abstract::A winter flounder antifreeze polypeptide (HPLC-6) has been studied in vacuo and in aqueous solution using molecular dynamics computer simulation techniques. The helical conformation of this polypeptide was found to be stable both in vacuum and in solution. The major stabilizing interactions were found to be the main-c...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360331002

    authors: McDonald SM,Brady JW,Clancy P

    更新日期:1993-10-01 00:00:00

  • Effect of chain length of HAV-VP3 synthetic peptides on its interaction with biomembrane models.

    abstract::Shorter analogues of a continuous epitope of hepatitis A virus, VP3(110-121) peptide, failed to react with convalescent sera, indicating the importance of the entire peptide in the epitope structure. To better understand the influence of the structural properties of this 12-mer peptide epitope on its biological activi...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(200012)54:7<477::AID-BIP10>3.0.C

    authors: Sospedra P,Muñoz M,García M,Alsina MA,Mestres C,Haro I

    更新日期:2000-12-01 00:00:00

  • Vibrational analysis of crystalline tri-L-alanine.

    abstract::We have found that tri-L-alanine (Ala3) can crystallize in a parallel-chain beta structure in addition to the previously known antiparallel-chain beta structure. Although the chain conformations in each structure are essentially similar, the ir and Raman spectra are distinctively different. We have calculated the norm...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360310208

    authors: Qian W,Bandekar J,Krimm S

    更新日期:1991-02-05 00:00:00

  • A quantum-dynamics study of the prototropic tautomerism of guanine and its contribution to spontaneous point mutations in Escherichia coli.

    abstract::High-level quantum-chemical and quantum-dynamics calculations are reported on the tautomerization equilibrium and rate constants of guanine and its complexes with one and two water molecules. The results are used to estimate the fraction of guanine present in the cell during DNA synthesis as the unwanted tautomer that...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(2001)61:1<77::AID-BIP10062>3.0.C

    authors: Gorb L,Podolyan Y,Leszczynski J,Siebrand W,Fernández-Ramos A,Smedarchina Z

    更新日期:2001-01-01 00:00:00

  • Energetic aspects of locked nucleic acids quadruplex association and dissociation.

    abstract::The design of modified nucleic acid aptamers is improved by considering thermodynamics and kinetics of their association/dissociation processes. Locked Nucleic Acids (LNA) is a promising class of nucleic acid analogs. In this work the thermodynamic and kinetic properties of a LNA quadruplex formed by the TGGGT sequenc...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20591

    authors: Petraccone L,Erra E,Randazzo A,Giancola C

    更新日期:2006-12-15 00:00:00

  • Prediction of a 12-residue loop in bovine pancreatic trypsin inhibitor: effects of buried water.

    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

    authors: Carlacci L

    更新日期:2001-04-05 00:00:00

  • 13 C solid-state NMR study of the 13 C-labeled peptide, (E)8 GGLGGQGAG(A)6 GGAGQGGYGG as a model for the local structure of Nephila clavipes dragline silk (MaSp1) before and after spinning.

    abstract::We prepared the water soluble model peptide, (E)(8) GGLGGQGAG(A)(6) GGAGQGGYGG, to throw light on the local structure of spidroin 1 (MaSpl) protein in spider dragline silk of Nephila clavipes before and after spinning. Solution (13) C NMR showed that the conformation of the peptide in aqueous solution was essentially ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21718

    authors: Yazawa K,Yamaguchi E,Knight D,Asakura T

    更新日期:2012-06-01 00:00:00

  • Terminal sidechain packing of a designed beta-hairpin influences conformation and stability.

    abstract::While end capping in alpha-helices is well understood, the concept of capping a beta-hairpin is a relatively recent development; to date, favorable Coulombic interactions are the only example of sidechains at the termini influencing the overall stability of a beta-hairpin. While cross-strand hydrophobic residues gener...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21177

    authors: Eidenschink L,Crabbe E,Andersen NH

    更新日期:2009-07-01 00:00:00

  • Molecular basis of the structural stability of hemochromatosis factor E: A combined molecular dynamic simulation and GdmCl-induced denaturation study.

    abstract::Hemochromatosis factor E (HFE) is a member of class I MHC family and plays a significant role in the iron homeostasis. Denaturation of HFE induced by guanidinium chloride (GdmCl) was measured by monitoring changes in [θ]222 (mean residue ellipticity at 222 nm), intrinsic fluorescence emission intensity at 346 nm (F346...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22760

    authors: Khan P,Parkash A,Islam A,Ahmad F,Hassan MI

    更新日期:2016-03-01 00:00:00

  • Structure-function correlation of outer membrane protein porin from Paracoccus denitrificans.

    abstract::Porins from outer membrane of Gram-negative bacteria have a highly stable structure. Our previous studies on porin from Paracoccus denitrificans showed that the outer membrane protein porin is extremely stable toward heat, pH, and chemical denaturants. The major question we have addressed in this paper is whether the ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20422

    authors: Sukumaran S,Hauser K,Maier E,Benz R,Mäntele W

    更新日期:2006-07-01 00:00:00