Air oxidation method employed for the disulfide bond formation of natural and synthetic peptides.

Abstract:

:Among the available protocols, chemically driven approaches to oxidize cysteine may not be required for molecules that, under the native-like conditions, naturally fold in conformations ensuring an effective pairing of the right disulfide bridge pattern. In this contest, we successfully prepared the distinctin, a natural heterodimeric peptide, and some synthetic cyclic peptides that are inhibitors of the CXCR4 receptor. In the first case, the air oxidation reaction allowed to connect two peptide chains via disulfide bridge, while in the second case allowed the cyclization of rationally designed peptides by an intramolecular disulfide bridge. Computational approaches helped to either drive de-novo design or suggest structural modifications and optimal oxidization protocols for disulfide-containing molecules. They are able to both predict and to rationalize the propensity of molecules to spontaneously fold in suitable conformations to achieve the right disulfide bridges.

journal_name

Amino Acids

journal_title

Amino acids

authors

Calce E,Vitale RM,Scaloni A,Amodeo P,De Luca S

doi

10.1007/s00726-015-1983-4

subject

Has Abstract

pub_date

2015-08-01 00:00:00

pages

1507-15

issue

8

eissn

0939-4451

issn

1438-2199

journal_volume

47

pub_type

杂志文章
  • Real-time heterogeneous protein-protein interaction between αA-crystallin N-terminal mutants and αB-crystallin using quartz crystal microbalance (QCM).

    abstract::The lens transparency depends on higher concentration of lens proteins and their interactions. α-Crystallin is one of the predominant lens proteins, responsible for proper structural and functional architecture of the lens microenvironment, and any alteration of which results in cataract formation. The R12C, R21L, R49...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-1935-z

    authors: Ramkumar S,Fujii N,Sakaue H,Fujii N,Thankappan B,kumari RP,Natarajaseenivasan K,Anbarasu K

    更新日期:2015-05-01 00:00:00

  • Transglutaminases: future perspectives.

    abstract::This is the third special issue focused on "Transglutaminases" that is now available on this journal and dedicated to one of the pioneers of these enzymes, John Edward Folk, who died December 2010 [see in this issue Beninati et al. 2012a]. The first edition, "Polyamines and Transglutaminases" was published in Amino Ac...

    journal_title:Amino acids

    pub_type: 社论

    doi:10.1007/s00726-012-1431-7

    authors: Beninati S,Facchiano F,Piacentini M

    更新日期:2013-01-01 00:00:00

  • Optimization of hydrolysis conditions, isolation, and identification of neuroprotective peptides derived from seahorse Hippocampus trimaculatus.

    abstract::Hippocampus trimaculatus is one of the most heavily traded seahorse species for traditional medicine purposes in many countries. In the present study, we showed neuroprotective effects of peptide derived from H. trimaculatus against amyloid-β42 (Aβ42) toxicity which are central to the pathogenesis of Alzheimer's disea...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1510-4

    authors: Pangestuti R,Ryu B,Himaya S,Kim SK

    更新日期:2013-08-01 00:00:00

  • Use ofα-aminoisobutyric acid and isovaline as marker amino acids for the detection of fungal polypeptide antibiotics. Screening ofHypocrea.

    abstract::Filamentous fungi of the genusHypocrea were grown on malt extract/peptone agar, the mycelia were extracted with dichloromethane/methanol, and the extracts were totally hydrolyzed with 6 N HCl (110°C, 24 h). The amino acids (AA) released from peptides were converted into theirN(O)-pen-tafluoropropionyl 1-propyl esters ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00806923

    authors: Brückner H,Maisch J,Reinecke C,Kimonyo A

    更新日期:1991-06-01 00:00:00

  • Functional significance of eIF5A and its hypusine modification in eukaryotes.

    abstract::The unusual basic amino acid, hypusine [N(epsilon)-(4-amino-2-hydroxybutyl)-lysine], is a modified lysine with the addition of the 4-aminobutyl moiety from the polyamine spermidine. This naturally occurring amino acid is a product of a unique posttranslational modification that occurs in only one cellular protein, euk...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-009-0408-7

    authors: Park MH,Nishimura K,Zanelli CF,Valentini SR

    更新日期:2010-02-01 00:00:00

  • A comparative study of the chemical reactivity of pyridoxamine, Ac-Phe-Lys and Ac-Cys with various glycating carbonyl compounds.

    abstract::Pyridoxamine (PM) has long been known to inhibit protein glycation via various mechanisms of action. One such mechanism involves the scavenging of carbonyl compounds with glycating ability. Despite the abundant literature on this topic, few quantitative kinetic studies on the processes involved have been reported. In ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-008-0098-6

    authors: Adrover M,Vilanova B,Frau J,Muñoz F,Donoso J

    更新日期:2009-03-01 00:00:00

  • Screening system for D-Asp-containing proteins using D-aspartyl endopeptidase and two-dimensional gel electrophoresis.

    abstract::D-Asp-containing proteins have been implicated in many aging-related diseases. To clarify the role of D-Asp-containing proteins in such diseases, we developed a screening system for these proteins using a D-aspartyl endopeptidase that specifically cleaves the proteins at the C-terminus. The digested proteins were dete...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-008-0040-y

    authors: Sakai-Kato K,Kinouchi T,Fujii N,Imai K,Utsunomiya-Tate N

    更新日期:2009-01-01 00:00:00

  • Short peptide constructs mimic agonist sites of AT(1)R and BK receptors.

    abstract::Extracellular peptide ligand binding sites, which bind the N-termini of angiotensin II (AngII) and bradykinin (BK) peptides, are located on the N-terminal and extracellular loop 3 regions of the AT(1)R and BKRB(1) or BKRB(2) G-protein-coupled receptors (GPCRs). Here we synthesized peptides P15 and P13 corresponding to...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1405-9

    authors: Lopes DD,Vieira RF,Malavolta L,Poletti EF,Shimuta SI,Paiva AC,Schreier S,Oliveira L,Nakaie CR

    更新日期:2013-03-01 00:00:00

  • Piceatannol attenuates homocysteine-induced endoplasmic reticulum stress and endothelial cell damage via heme oxygenase-1 expression.

    abstract::A growing body of evidence implicates endoplasmic reticulum (ER)-induced cellular dysfunction and apoptosis as important factors to a variety of diseases. In endothelial cells (ECs), the sulfur-containing amino acid homocysteine (Hcy) causes EC apoptosis and reactive oxygen species (ROS) generation through induction o...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-016-2375-0

    authors: Kil JS,Jeong SO,Chung HT,Pae HO

    更新日期:2017-04-01 00:00:00

  • Nutritionally non-essential amino acids are dispensable for whole-body protein synthesis after exercise in endurance athletes with an adequate essential amino acid intake.

    abstract::The increased protein requirement of endurance athletes may be related to the need to replace exercise-induced oxidative losses, especially of the branched-chain amino acids (BCAA). However, it is unknown if non-essential amino acids (NEAA) influence the requirement for essential amino acids (EAA) during post-exercise...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2639-y

    authors: Kato H,Volterman KA,West DWD,Suzuki K,Moore DR

    更新日期:2018-12-01 00:00:00

  • A refined synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids.

    abstract::The synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids has been refined to improve both the efficiency and the simplicity. These improvements provide a shorter and easier access to the racemic cis-cyclobutane β-amino acid core. Derivatization of this material with a chiral non-racemic oxazolidin-2-o...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-0918-y

    authors: Declerck V,Aitken DJ

    更新日期:2011-08-01 00:00:00

  • Free amino acids and biogenic amines in red and white muscle of tuna stored in controlled atmospheres.

    abstract::This paper analyses the presence of and changes in free amino acids and biogenic amines in red and white muscle of bigeye tuna during storage in controlled atmospheres with 2 gas mixes containing different concentrations of CO(2) and O(2). Levels of amines were generally higher in white than in red muscle, with the ex...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-003-0054-4

    authors: Ruiz-Capillas C,Moral A

    更新日期:2004-03-01 00:00:00

  • Nucleobase-containing peptides: an overview of their characteristic features and applications.

    abstract::Reports on nucleobase-containing chiral peptides (both natural and artificial) and achiral pseudopeptides are reviewed. Their synthesis, structural features, DNA and RNA-binding ability, as well as some other interesting applications which make them promising diagnostic/therapeutic agents of great importance in many a...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-010-0567-6

    authors: Roviello GN,Benedetti E,Pedone C,Bucci EM

    更新日期:2010-06-01 00:00:00

  • Correction to: Human baby hair amino acid natural abundance 15N-isotope values are not related to the 15N-isotope values of amino acids in mother's breast-milk protein.

    abstract::In the article (Romek et al. 2013) we reported the values of δ15N (‰) and δ13C (‰) obtained by. ...

    journal_title:Amino acids

    pub_type: 杂志文章,已发布勘误

    doi:10.1007/s00726-017-2506-2

    authors: Romek KM,Julien M,Frasquet-Darrieux M,Tea I,Antheaume I,Hankard R,Robins RJ

    更新日期:2018-01-01 00:00:00

  • Determination of the protooncogene ets-2 gene transcript in human brain at the atto-gram-level by the use of competitive RT/PCR.

    abstract::Protooncogenes (PO) play a crucial role for brain biology and pathology. Only the concerted action of protooncogenes enables normal brain development. The reliable and sensitive quantification of brain PO is still holding centre stage in neurobiological research. The aim of our study was therefore the determination of...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF01318881

    authors: Schatzmann-Turhani D,Greber-Platzer S,Cairns N,Lubec G

    更新日期:1999-01-01 00:00:00

  • A synthetic peptide derived of the β2-β3 loop of the plant defensin from Vigna unguiculata seeds induces Leishmania amazonensis apoptosis-like cell death.

    abstract::For medical use of proteins and peptide-based drugs, it is desirable to have small biologically active sequences because they improve stability, reduce side effects, and production costs. Several plant defensins have their biological activities imparted by a sequence named γ-core. Vu-Def, a Vigna unguiculata defensin,...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-019-02800-8

    authors: Souza GS,de Carvalho LP,de Melo EJT,da Silva FCV,Machado OLT,Gomes VM,de Oliveira Carvalho A

    更新日期:2019-11-01 00:00:00

  • CCK and NPY as anti-anxiety treatment targets: promises, pitfalls, and strategies.

    abstract::Short CCK peptides elicit panic attacks in humans and anxiogenic-like effects in some animal models, but CCK receptor antagonists have not been found clinically effective. Yet CCK overactivity appears to be involved in submissive behaviour, and CCKB receptor expression and binding are increased in suicide victims and ...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-006-0334-x

    authors: Harro J

    更新日期:2006-10-01 00:00:00

  • Molecular imaging of perfusion disturbances in glaucoma.

    abstract::Ocular ischemia resulting from perfusion disturbances may play a major role in initiation of glaucoma. Possibly secondary to ischemia autoimmunogenic events are activated in glaucoma patients with increased prevalence of systemic autoimmune diseases. The determination of potential molecular markers in blood leukocytes...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-001-0141-3

    authors: Golubnitschaja O,Wunderlich K,Decker C,Mönkemann H,Schild HH,Flammer J

    更新日期:2002-01-01 00:00:00

  • A fusion antitumor peptide regulates proliferation and apoptosis of endothelial cells.

    abstract::The present research has been carried out to elicit the mechanism of antiangiogenic activity of a fusion peptide P2. Peptide P2 was designed by the connection of a heptapeptide MMP inhibitor to ES-2, a fragment of Endostatin. In a previous study, P2 demonstrated strong antiangiogenic and antitumor effect, and the curr...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2589-4

    authors: Xu Y,Qiang X,Xing L,Wang H,Zhang J,Zhang F,Caliskan B,Wang M,Qiu Z

    更新日期:2018-08-01 00:00:00

  • Adenosine receptor agonists affect taurine release from mouse brain stem slices in ischemia.

    abstract::The release of the inhibitory amino acid taurine is markedly enhanced under ischemic conditions in both adult and developing brain stem, together with a pronounced increase in the release of the neuromodulator adenosine. We now studied the effects of adenosine receptor agonists and antagonists on [(3)H]taurine release...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0351-7

    authors: Saransaari P,Oja SS

    更新日期:2010-05-01 00:00:00

  • Spermine oxidase: ten years after.

    abstract::Spermine oxidase (SMO) was discovered much more recently than other enzymes involved in polyamine metabolism; this review summarizes 10 years of researches on this enzyme. Spermine oxidase (SMO) is a FAD-dependent enzyme that specifically oxidizes spermine (Spm) and plays a dominant role in the highly regulated mammal...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-011-1014-z

    authors: Cervelli M,Amendola R,Polticelli F,Mariottini P

    更新日期:2012-02-01 00:00:00

  • The designer leptin antagonist peptide Allo-aca compensates for short serum half-life with very tight binding to the receptor.

    abstract::The leptin receptor antagonist peptide Allo-aca exhibits picomolar activities in various cellular systems and sub-mg/kg subcutaneous efficacies in animal models making it a prime drug candidate and target validation tool. Here we identified the biochemical basis for its remarkable in vivo activity. Allo-aca decomposed...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1650-6

    authors: Otvos L Jr,Vetter SW,Koladia M,Knappe D,Schmidt R,Ostorhazi E,Kovalszky I,Bionda N,Cudic P,Surmacz E,Wade JD,Hoffmann R

    更新日期:2014-04-01 00:00:00

  • The effect of lysine deprivation on leukemic blood.

    abstract::Studies have shown that specific amino acids are required for optimal growth of leukemic versus normal cells, and it is believed that the depletion of selected amino acids can abrogate tumor growth. We have developed a technique for studying the effect of amino acid deprivation on leukemic cell proliferation. The tech...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00805995

    authors: Reiken SR,Briedis DM

    更新日期:1992-10-01 00:00:00

  • Profiling of residue-level photo-oxidative damage in peptides.

    abstract::Protein and peptide oxidation is a key feature in the progression of a variety of disease states and in the poor performance of protein-based products. The present work demonstrates a mass spectrometry-based approach to profiling degradation at the amino acid residue level. Synthetic peptides containing the photosensi...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0440-7

    authors: Grosvenor AJ,Morton JD,Dyer JM

    更新日期:2010-06-01 00:00:00

  • The therapeutic and nutraceutical potential of agmatine, and its enhanced production using Aspergillus oryzae.

    abstract::Agmatine, a natural polyamine produced from arginine by arginine decarboxylase, was first discovered in 1910, but its physiological significance was disregarded for a century. The recent rediscovery of agmatine as an endogenous ligand for α2-adrenergic and imidazoline receptors in the mammalian brain suggests that thi...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-019-02720-7

    authors: Akasaka N,Fujiwara S

    更新日期:2020-02-01 00:00:00

  • Characterization of calmodulin binding domains in TRPV2 and TRPV5 C-tails.

    abstract::The transient receptor potential channels TRPV2 and TRPV5 belong to the vanilloid TRP subfamily. TRPV2 is highly similar to TRPV1 and shares many common properties with it. TRPV5 (and also its homolog TRPV6) is a rather distinct member of the TRPV subfamily. It is distant for being strictly Ca(2+)-selective and featur...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-010-0712-2

    authors: Holakovska B,Grycova L,Bily J,Teisinger J

    更新日期:2011-02-01 00:00:00

  • Amino acids and gut function.

    abstract::The intestine is not only critical for the absorption of nutrients, but also interacts with a complex external milieu. Most foreign antigens enter the body through the digestive tract. Dietary amino acids are major fuels for the small intestinal mucosa, as well as important substrates for syntheses of intestinal prote...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-008-0152-4

    authors: Wang WW,Qiao SY,Li DF

    更新日期:2009-05-01 00:00:00

  • Taurine promotes connective tissue growth factor (CTGF) expression in osteoblasts through the ERK signal pathway.

    abstract::Taurine is found in bone tissue, but its function in skeletal tissue is not fully understood. The present study was undertaken to investigate regulation of gene expression of connective tissue growth factor (CTGF), and the roles of mitogen-activated protein kinases (MAPKs) in murine osteoblast MC3T3-E1 cells treated w...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-006-0380-4

    authors: Yuan LQ,Lu Y,Luo XH,Xie H,Wu XP,Liao EY

    更新日期:2007-01-01 00:00:00

  • Catabolism of native and oxidized low density lipoproteins: in vivo insights from small animal positron emission tomography studies.

    abstract::The human organism is exposed to numerous processes that generate reactive oxygen species (ROS). ROS may directly or indirectly cause oxidative modification and damage of proteins. Protein oxidation is regarded as a crucial event in the pathogenesis of various diseases ranging from rheumatoid arthritis to Alzheimer's ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-005-0203-z

    authors: Pietzsch J,Bergmann R,Wuest F,Pawelke B,Hultsch C,van den Hoff J

    更新日期:2005-12-01 00:00:00

  • Transglutaminases and receptor tyrosine kinases.

    abstract::Transglutaminases are confounding enzymes which are known to play key roles in various cellular processes. In this paper, we aim to bring together several pieces of evidence from published research and literature that suggest a potentially vital role for transglutaminases in receptor tyrosine kinases (RTK) signalling....

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-011-1113-x

    authors: Sivaramakrishnan M,Shooter GK,Upton Z,Croll TI

    更新日期:2013-01-01 00:00:00