bluuebunny/crossref_metadata_2025_split huggingface dataset:
Building a bridge between peptide chemistry and organic chemistry: Intramolecular macrocyclization reactions and supramolecular chemistry with helical peptide substrates
Authors: Moretto Alessandro , Crisma Marco , Formaggio Fernando , Toniolo Claudio 
Published: August 2010

AbstractIn our ongoing efforts to build a bridge between peptide chemistry and organic chemistry, we are currently investigating: (1) two types of intramolecular macrocyclization reactions in 310‐helical peptides, and (2) a peptido[2]rotaxane molecular machine as a supramolecular tool using a 310‐helical peptide as the axle. More specifically, we studied the following two reactions: (a) the intramolecular ring‐closing olefin metathesis between two amino acid residues with side chains bearing an allyl group, and (b) the intramolecular Paternò‐Yang photoreaction, using a benzophenone‐based amino acid as a photoaffinity reagent for a Met residue. Both reactions involve formation of a new CC bond. As for the supramolecular system examined, we were able to identify the two stations of a new peptido[2]rotaxane characterized by an ‐(Aib)6‐ axle and to reversibly switch the aromatic tetramide macrocyclic wheel from one station to the next. This article summarizes the information available in the literature from other groups and the published/unpublished data originated from our laboratory on these research areas. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 94: 721–732, 2010.This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com
Synthetic diastereomeric‐antimicrobial peptide: Antibacterial activity against multiple drug resistant clinical isolates
Authors: Park Seong‐Cheol , Kim Jin‐Young , Lee Jong‐Kook , Yoo Suyeon , Kim Hyunjoong , Seo Chang Ho , Nah Jae‐Woon , Hahm Kyung‐Soo , Park Yoonkyung 
Published: August 2010

AbstractIncreasing resistance of pathogenic bacteria to antibiotics is a serious problem in health care system and has intensified the search for potent novel drugs. Cationic antibacterial peptides are the most abundant antibiotics in nature and have been frequently proposed as new anti‐infective agents. In this study, a set of diastereomeric peptides is researched about their antibiotic activity against multiple drug resistant clinical isolates and their modes of action against gram‐positive cocci. MIC was suggested by the NCCLS against ten clinically isolated antibiotic‐resistant strains. Mode of action studies included killing kinetics and a series of experiments designed to characterize the impact of the diastereomeric peptides on bacterial membranes. The tested diastereomers displayed high antimicrobial and broad spectrum activity with D‐P5‐18mer. The antimicrobial activity of diastereomeric‐P5‐18mer was two times stronger against gram‐negative bacteria than either CA‐MA‐20mer or P5‐18mer. When tested against ten clinically isolated antibiotic‐resistant strains in the presence of 0, 150, or 300 mM NaCl, diastereomeric‐P5‐18mer retained strong activity against all bacteria, yet showed little or no cytotoxicity against the HaCaT human keratinocyte cell line. Finally, D‐P5‐18mer showed resistance against trypsin digestion unlike other analogues. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 96: 130–136, 2011.
Native chemical ligation with Nα acyl transfer auxiliaries
Authors: Offer John 
Published: August 2010

AbstractNative chemical ligation (NCL) is a simple procedure that enables synthetic access to many proteins and is increasingly harnessed to study protein structure and function. However, the generality of this method is limited by the requirement for cysteine residues suitably positioned throughout the target protein. Auxiliary approaches have been developed to overcome this limitation, wherein a removable group is introduced at the amino terminus of a peptide conveying ligation properties comparable to cysteine. Present auxiliary approaches combine the thioester exchange concept applied first in NCL with a number of acyl transfer reactions first systematically explored by Kemp and coworkers. The current methods for auxiliary mediated ligation appear promising for the synthesis of proteins and in particular post‐translational modified proteins. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 94: 530–541, 2010.
Posttranslationally modified peptides efficiently mimicking neoantigens: A challenge for theragnostics of autoimmune diseases
Authors: Nuti Francesca , Peroni Elisa , Real‐Fernández Feliciana , Bonache M. Angeles , Le Chevalier‐Isaad Alexandra , Chelli Mario , Lubin‐Germain Nadège , Uziel Jacques , Rovero Paolo , Lolli Francesco , Papini Anna Maria 
Published: August 2010

AbstractWe report the design, synthesis, and immunological evaluation of a series of glycopeptide analogues of the previously described antigenic probe CSF114(Glc), with the aim of understanding the importance of N‐glycosylation on Asn residue in multiple sclerosis antibody recognition. The glucopeptide, characterized by a β‐turn conformation which is fundamental for a correct presentation of the epitope, has been modified by introducing various natural glycoamino acids in position 7. The new glycopeptides were evaluated by measuring the IgG and IgM antibody titer in multiple sclerosis patients' and normal blood donors' sera. Moreover, we achieved the efficient synthetic strategy of new Asn derivative bearing N‐acetylneuraminic acid (Neu5Ac), linked by an N‐glycosidic bond, on the side chain of the Asn residue orthogonally protected for Fmoc/tBu SPPS. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 94: 791–799, 2010.This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com
The influence of incorporating lipids or liposaccharides on the particle size of peptide therapeutics
Authors: Coles Daniel J. , Simerska Pavla , Fujita Yoshio , Toth Istvan 
Published: August 2010

AbstractThe characterization of peptide‐based drugs is essential to obtain information about their potential suitability. In this study, a therapeutic peptide epitope alone or in combination with a lipid or liposaccharide moiety were assessed to determine their particle sizes by diffusion ordered NMR spectroscopy, dynamic light scattering, and mathematical expressions. These methods were compared and their suitability for different types of peptides is discussed herein. When compared with the mathematical expressions, we found that the NMR method resulted in a particle size that was consistent with the radius of the peptide monomer. The dynamic light scattering method showed that when lipids were conjugated to the peptide epitope, the resulting particles had a larger sized distribution compared with the peptide alone. These experiments provided information which can be applied when formulating these peptides as drugs. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 96: 172–176, 2011.
Design and conformational analysis of natively folded β‐hairpin peptides stabilized by nucleobase interactions
Authors: Uozumi Ryuichi , Takahashi Tsuyoshi , Yamazaki Toshimasa , Granholm Viktor , Mihara Hisakazu 
Published: August 2010

AbstractTo examine stabilizing effects of the base pair interaction on a protein scaffold, various peptides with L‐α‐amino acids bearing a nucleobase in the side chain (nucleobase amino acids; NBAs) were designed based on a G‐peptide β‐hairpin structure, and their conformational properties were investigated by circular dichroism and NMR spectroscopy. Thermodynamic analyses based on the chemical shifts showed that adenine‐thymine pairing in a diagonal fashion at positions 4 and 15 (2AT) enhanced thermal stability of the peptide conformation by more than 30 K as compared with the wild‐type G‐peptide. In NOESY spectrum, not only numerous nonadjacent crosspeaks but also long‐range crosspeaks between the nucleobases were observed in some peptides with the base pairing. NMR structure calculations of the 2AT peptide confirmed that cross‐strand pairing of the nucleobases occurs on the well‐defined β‐hairpin structure as designed. Taken together, the base pairing in an appropriate position and orientation facilitates folding and stabilization of a native‐like β‐hairpin structure. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 94: 830–842, 2010.This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com
Design and development of analogues of dimers of insulin‐like peptide 3 B‐chain as high‐affinity antagonists of the RXFP2 receptor
Authors: Shabanpoor Fazel , Zhang Suode , Hughes Richard A. , Hossain Mohammed Akhter , Layfield Sharon , Ferraro Tania , Bathgate Ross A. D. , Separovic Frances , Wade John D. 
Published: August 2010

AbstractInsulin‐like peptide 3 (INSL3) is one of 10 members of the human relaxin–insulin superfamily of peptides. It is a peptide hormone that is expressed by fetal and postnatal testicular Leydig cells and postnatal ovarian thecal cells. It mediates testicular descent during fetal life and suppresses sperm apoptosis in adult males, whereas, in females, it causes oocyte maturation. INSL3 has also been shown to promote thyroid tumor growth and angiogenesis in human. These actions of INSL3 are mediated through its G protein‐coupled receptor, RXFP2. INSL3, a two‐chained peptide, binds to its receptor primarily via its B‐chain, whereas elements of the A‐chain are essential for receptor activation. In an attempt to design a high‐affinity antagonist with potential clinical application as an anticancer agent as well as a contraceptive, we have previously prepared a synthetic parallel dimer of INSL3 B‐chain and demonstrated that it binds to RXFP2 with high affinity. In this work, we undertook full pharmacological characterization of this peptide and show that it can antaogonize INSL3‐mediated cAMP signaling through RXFP2. Further refinement by truncation of 18 residues yielded a minimized analogue that retained full binding affinity and INSL3 antagonism. It is an attractive lead peptide for in vivo evaluation as an inhibitor of male and female fertility and of INSL3‐mediated carcinogenesis. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 96: 81–87, 2011.
Deletion of Ac‐NMePhe1 from [NMePhe1]arodyn under acidic conditions, part 2: Effects of cleavage conditions and N‐terminal functionality
Authors: Fang Wei‐Jie , Bennett Marco A. , Aldrich Jane V. 
Published: August 2010

AbstractPeptides containing N‐methylamino acids can exhibit improved pharmacodynamic and pharmacokinetic profiles compared to nonmethylated peptides, and therefore interest in these N‐methylated peptides has been increasing in recent years. Arodyn (Ac[Phe1,2,3,Arg4,D‐Ala8]Dyn A(1–11)NH2) is an acetylated dynorphin A (Dyn A) analog that is a potent and selective κ opioid receptor antagonist (Bennett et al., J Med Chem 2002, 45, 5617), and its analog [NMePhe1]arodyn shows even higher affinity and selectivity for κ opioid receptors (Bennett et al., J Pept Res 2005, 65, 322). During the synthesis of [NMePhe1]arodyn analogs, the arodyn‐(2–11) derivatives were obtained as major products. Analysis indicated that Ac‐NMePhe was lost from the completed peptide sequence during acidic cleavage of the peptides from the resin and that the acetyl group played an important role in this side reaction. Different cleavage conditions were evaluated to minimize this side reaction and maximize the yield of pure [NMePhe1]arodyn analogs. Modifications to the N‐terminus of the peptides to prevent the side reaction were also explored. The incorporation of a heteroatom‐containing group such as methoxycarbonyl as the N‐terminal functionality prevented this side reaction, while the incorporation of a bulky acyl group could not. Substituting NMePhe with the conformationally constrained analog Tic (1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylic acid) also prevented the side reaction. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 96: 97–102, 2011.
p‐Nitrobenzyl protection for cysteine and selenocysteine: A more stable alternative to the acetamidomethyl group
Authors: Muttenthaler Markus , Ramos Yesica Garcia , Feytens Debby , de Araujo Aline D. , Alewood Paul F. 
Published: August 2010

AbstractThis study evaluated the acidic lability of the acetamidomethyl (Acm), trimethylacetamidomethyl (Tacm), and thep‐nitrobenzyl (pNB) as protecting groups for cysteine and selenocysteine (Sec) during thetert‐butyloxycarbonyl (Boc)‐chemistry solid‐phase peptide synthesis of oxytocin (OT). Two novel Sec building blocks (Nα‐tert‐butyloxycarbonyl‐Se(acetamidomethyl)‐L‐selenocysteine (Boc‐L‐Sec(Acm)‐OH) andNα‐tert‐butyloxycarbonyl‐S(4‐nitrobenzyl)‐L‐selenocysteine (Boc‐L‐Sec(pNB)‐OH)) were developed for this study. Six partially protected thio‐ and seleno‐OT analogues were synthesized, purified, and exposed to neat trifluoroacetic acid (TFA) at temperatures of 25, 40, 50, and 60°C for 1 h, and HF treatment at 0°C for 1 h. Significant losses were observed for the Acm and Tacm group in TFA at temperatures greater than 25°C and during HF treatment at 0°C, whereas thepNB group remained intact. Removal of thepNB was achieved via reduction to thep‐aminobenzyl group either with zinc in acetic acid in solution or via tin chloride in hydrochloric acid on solid support, followed by oxidative cleavage with iodine yielding the corresponding disulfide or diselenide bond. No major side reactions were observed. This study confirms the occasionally described Acm instability and underpins the development of thepNB group as an alternative for cysteine and Sec protection. © 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 94: 423–432, 2010.
Water Stable Zr–Benzenedicarboxylate Metal–Organic Frameworks as Photocatalysts for Hydrogen Generation
Authors: Gomes Silva Cláudia , Luz Ignacio , Llabrés i Xamena Francesc X. , Corma Avelino , García Hermenegildo 
Published: August 2010

AbstractThe Zr‐containing metal–organic frameworks (MOFs) formed by terephthalate (UiO‐66) and 2‐aminoterephthalate ligands [UiO‐66(NH2)] are two notably water‐resistant MOFs that exhibit photocatalytic activity for hydrogen generation in methanol or water/methanol upon irradiation at wavelength longer than 300 nm. The apparent quantum yield for H2 generation using monochromatic light at 370 nm in water/methanol 3:1 was of 3.5 % for UiO‐66(NH2). Laser‐flash photolysis has allowed detecting for UiO‐66 and UiO‐66(NH2) the photochemical generation of a long lived charge separated state whose decay is not complete 300 μs after the laser flash. Our finding and particularly the influence of the amino group producing a bathochromic shift in the optical spectrum without altering the photochemistry shows promises for the development of more efficient MOFs for water splitting.
Synthesis and Conformational Characterisation of Hexameric β‐Peptide Foldamers by Using Double POAC Spin Labelling and cw‐EPR
Authors: Wright Karen , Wakselman Michel , Mazaleyrat Jean‐Paul , Franco Lorenzo , Toffoletti Antonio , Formaggio Fernando , Toniolo Claudio 
Published: August 2010

AbstractA selected set of terminally protected β‐hexapeptides, each containing two nitroxide‐based (3R,4R)‐4‐amino‐1‐oxyl‐2,2,5,5‐tetramethylpyrrolidine‐3‐carboxylic acid (POAC) residues combined with four (1S,2S)‐2‐aminocyclopentane‐1‐carboxylic acid (ACPC) residues, was synthesised by using solution methods and was fully characterised. The two POAC residues are separated in the sequences by different numbers of intervening ACPC residues. The conformational features of the doubly spin‐labelled β‐hexapeptides were examined in chloroform by FTIR absorption and continuous‐wave electron paramagnetic resonance spectroscopic techniques. In particular, the biradical exchange coupling (J) between two POAC residues within each peptide indicates unambiguously that the secondary structure overwhelmingly adopted is the 12‐helix. Taken together, these results support the view that POAC is an excellent β‐amino acid for exploring this type of helical conformation in doubly labelled β‐peptides.
ChemInform Abstract: Na8Au11In6: A Gold Indium Polyhedra Framework with Pentagonal Bipyramidal AuAu5In Building Units.
Authors: ZACHWIEJA U. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: A New Layer‐Structured Nitride Superconductor. Lithium‐Intercalated β‐Zirconium Nitride Chloride, LixZrNCl.
Authors: YAMANAKA S. , KAWAJI H. , HOTEHAMA K. , OHASHI M. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Nickel Catalysts for Internal Reforming in Molten Carbonate Fuel Cells
Authors: BERGER R. J. , DOESBURG E. B. M. , VAN OMMEN J. G. , ROSS J. R. H. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Synthesis and Structure of Cyclic Selenium Oxide SeVISeIV2O7.
Authors: TOUZIN J. , KILIAN P. , ZAK Z. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Ground‐State Stereoelectronic Effects Involving Silicon and Germanium: A Comparison of the Effects of Germanium and Silicon Substituents on C‐ O Bond Lengths at the β‐Position.
Authors: CHAN V. Y. , CLARK C. I. , GIORDANO J. , GREEN A. J. , KARALIS A. , WHITE J. M. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Soluble Polymer‐Bound Ligand‐Accelerated Catalysis: Asymmetric Dihydroxylation.
Authors: HAN H. , JANDA K. D. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Intramolecular (2 + 2) Photocycloaddition of N‐Alkenoyl‐β‐ enaminones.
Authors: AMOUGAY A. , PETE J.‐P. , PIVA O. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Synthesis of a Water‐Soluble Conjugated (3)Rotaxane.
Authors: ANDERSON S. , ANDERSON H. L. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Synthesis of (.+‐.)‐trans‐Cyclopropane‐1,2‐N,N′‐dinitroamine and Its Derivatives
Authors: IVSHIN V. P. , KOMELIN M. S. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: A General and Convenient Synthetic Method of Geometrically Pure (Z)‐1‐ Bromo‐1‐alkenes.
Authors: UENISHI J. , KAWAHAMA R. , SHIGA Y. , YONEMITSU O. , TSUJI J. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Synthesis of Phenolic Biaryls and p‐Terphenyls and Their Heteroaromatic Analogues via a Cycloaddition Route Using 4‐Aryl‐2‐ silyloxybuta‐1,3‐dienes and Electron‐Deficient Alkynes.
Authors: YAMAMOTO Y. , NUNOKAWA K. , OHNO M. , EGUCHI S. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: The First Optically Active and Sterically Regular Poly(1,1′‐bi‐2‐ naphthol)s: Precursors to a New Generation of Polymeric Catalysts.
Authors: HU Q. S. , ZHENG X.‐F. , PU L. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Intramolecular 1,6‐Conjugate Addition Approach for Construction of the Hydrindan Framework: Total Synthesis of (.+‐.)‐Coronafacic Acid.
Authors: NARA S. , TOSHIMA H. , ICHIHARA A. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: Novel Enantioselective Approach to γ‐Lactams from Chiral Enol Ethers: Synthesis of (‐)‐Statine.
Authors: NEBOIS P. , GREENE A. E. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform Abstract: The Thermal Rearrangement of N‐Alkyl‐N‐vinylpropargylamines into 2‐ Methylpyrroles. A New Synthesis of Annulated(b)pyrroles.
Authors: COSSY J. , POITEVIN C. , SALLE L. , GOMEZ PARDO D. 
Published: August 2010

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.