Peptide Synthesis Applications

Gain insight into how Protein Technologies' platforms have been applied in research and development related to biomaterials, drug delivery, peptide therapeutics, vaccines and venoms & toxins.

Read our new article “Turning up the heat on peptide purity” in Chemistry Today to learn how:

  • Parallel synthesis optimization was performed on the Prelude X for the preparation of difficult and biologically active peptides
  • Optimized methods with induction heating can be used to achieve a 5-fold decrease in reaction time and 4-fold increase in crude purity

Read the article

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Therapeutics and Vaccines

Application Notes

Cost-Effective Automated Phosphopeptide Synthesis on the Prelude™ Using Single-Shot™ Deliveries

The use of specially modified amino acids is available for a wide variety of peptide synthesis applications. These modified monomers are frequently extremely expensive and their implementation is limited by these costs.

 

Posters

Multivariable Individual Heating Conditions Tested in Parallel Provide Rapid Process Optimization on Prelude X

The application of heat represents a useful tool to optimize the production of challenging synthetic peptides, and a new technology, induction heating, has been introduced on the Prelude X.

 

High-throughput parallel synthesis optimization of Glucagon-like Peptide 1 receptor agonists

Poster presented at EPS2018

 

Synthesis of therapeutic stapled peptides: Fully automated peptide cyclization via olefin metathesis

Poster presented at EPS2018

 

Publications

The Extracellular Surface of the GLP-1 Receptor Is a Molecular Trigger for Biased Agonism Cell.
Wootten D. et al. Cell. 2016 Jun 16; 165(7): 1632-1643.2016

Modular peptide amphiphile micelles improve an antibody-mediated immune response to Group A Streptococcus.
Barrett J.C. et al. ACS Biomater. Sci. Eng.2016

Substoichiometric inhibition of transthyretin misfolding by immune-targeting sparsely populated misfolding intermediates: a potential diagnostic and therapeutic for TTR amyloidoses.
Galant N.J. et al. Scientific Reports, 6, 25080.2016

Two Novel Dermaseptin-Like Antimicrobial Peptides with Anticancer Activities from the Skin Secretion of Pachymedusa dacnicolor.
Shi D. et al. Toxins, 8(5), 144.2016

The frequency of naive and early-activated hapten-specific B cell subsets dictates the efficacy of a therapeutic vaccine against prescription opioid abuse.
Laudenbach M. et al.  Journal of Immunology (Baltimore, Md.?: 1950), 194(12), 5926-5936. 2015

Design and characterization of ebolavirus GP prehairpin intermediate mimics as drug targets.
Clinton T.R. et al. Protein Science: A Publication of the Protein Society, 24(4), 446-463.2015

Peptide Amphiphile Micelles Self-Adjuvant Group A Streptococcal Vaccination.
Trent A. et al. The AAPS Journal, 17(2), 380-388.2015

Structural and antigenic features of the synthetic SF23 peptide corresponding to the receptor binding fragment of diphtheria toxin.
Khrustaleva T.A. et al.  Molecular immunology 63.2 (2015): 235-244.2015

Identification of key residues involved in adrenomedullin binding to the AM1 receptor
Watkins H. et al. British Journal of Pharmacology, 169(1), 143–155.2013

T1BT* structural study of an anti-plasmodial peptide through NMR and molecular dynamics
Topchiy E. et al. Malaria Journal, 12, 104.2013

Development of Potent and Metabolically Stable APJ Ligands with High Therapeutic Potential
Juhl C.et al. ChemMedChem 2016, 11, 2378.2016

The Human Autoantibody Response to Apolipoprotein A-I Is Focused on the C-Terminal Helix: A New Rationale for Diagnosis and Treatment of Cardiovascular Disease?
Pagano S. et al.  PLoS ONE 10(7): e01327802015

Design of a peptide inhibitor of tyrosine kinase 2
Works M.G. et al. Protein Pept Lett. 2014 May;21(5):419-252014

The impact of synthetic analogs of histidine on copper(II) and nickel(II) coordination properties to an albumin-like peptide. Possible leads towards new metallodrugs
Zawisza L. et al. J Inorg Biochem. 2014 Oct;139:1-82014

Immunogenicity Studies of Bivalent Inactivated Virions of EV71/CVA16 Formulated with Submicron Emulsion Systems
Lin C.-W. et al. BioMed Research International Volume 2014 (2014), Article ID 6705062014

Discovery and Characterization of a Potent Interleukin-6 Binding Peptide with Neutralizing Activity In Vivo
Ranganath S. et al. PLoS ONE, 10(11), e0141330.2015

In Vivo Efficacy of Anuran Trypsin Inhibitory Peptides against Staphylococcal Skin Infection and the Impact of Peptide Cyclization
Malik U. et al. Antimicrob Agents Chemother. 2015 Apr;59(4):2113-21.2015

Semienzymatic Cyclization of Disulfide-rich Peptides Using Sortase A
Jia X. et al. J Biol Chem. 2014 Mar 7;289(10):6627-38.2014

Immunogenicity in mice and non-human primates of the Group A Streptococcal J8 peptide vaccine candidate conjugated to CRM197
Caro-Aguilar I. et al. Hum Vaccin Immunother. 2013 Mar;9(3):488-96.2013

Synthesis and characterization of a high-affinity αvβ6-specific ligand for in vitro and in vivo applications.
Shunzi L. et al. Molecular Cancer Therapeutics, 8(5), 1239-1249.2009

Design of Potent and Selective Cathepsin G Inhibitors Based on the Sunflower Trypsin Inhibitor-1 Scaffold
Swedberg J.A. et al. J. Med. Chem. Publication Date (Web): January 3.2017

De-immunized and Functional Therapeutic (DeFT) versions of a long lasting recombinant alpha interferon for antiviral therapy
Mufarrege E.F. et al. Clinical Immunology Volume 176, March 2017, Pages 31–41.2017

DS6: anticandidal, antibiofilm peptide against Candida tropicalis and exhibit synergy with commercial drug
Singh K. et al. Journal of Peptide Science2017

5-LOX in Alzheimer's Disease: Potential Serum Marker and In Vitro Evidences for Rescue of Neurotoxicity by Its Inhibitor YWCS
Shekhar S. et al. Mol Neurobiol (2017). doi:10.1007/s12035-017-0527-1.2017

Selection and structural analysis of the NY25 peptide – A vaccine candidate from hemagglutinin of swine-origin Influenza H1N1
Khrustalev V. V. et al. Microbial Pathogenesis, Volume 125, December 2018, Pages 72-83.2018

Rapid and low-cost multiplex synthesis of chemokine analogs
Paolini-Bertrand M. et al JBC Papers in Press. Published on October 10, 2018 as Manuscript RA118.004370.2018

Oncology peptide therapeutics

Application Notes

Synthesis of [des-Arg7]-Dyn A (1-9)-NH2 peptoid hybrid

Automated solid phase peptide synthesis (SPPS) increases reliability, efficiency, and crude purity for peptides and peptoids.

 

Publications

Flexibility is important for inhibition of the MDM2/p53 protein-protein interaction by cyclic Beta-hairpins
Danelius E. et al. Org. Biomol. Chem., 2016,14, 10386-10393.2016

Serum Stability and Affinity Optimization of an M2 Macrophage-Targeting Peptide (M2pep).
Ngambenjawong C. et al. Theranostics, 6(9), 1403-1414.2016

A Peptide Mimicking a Region in Proliferating Cell Nuclear Antigen Specific to Key Protein Interactions Is Cytotoxic to Breast Cancer.
Smith S. J. et al. Molecular Pharmacology, 87(2), 263-276. 2015

Targeted therapy of colorectal neoplasia with rapamycin in peptide-labeled pegylated octadecyl lithocholate micelles.
Khondee S. et al. Journal of Controlled Release: Official Journal of the Controlled Release Society, 199, 114-121.2015

Targeted bioimaging and photodynamic therapy of cancer cells with an activatable red fluorescent bioprobe.
Hu Fang et al. Analytical chemistry 86.15 (2014): 7987-7995.2014

Simultaneous Inhibition of Key Growth Pathways in Melanoma Cells and Tumor Regression by a Designed Bidentate Constrained Helical Peptide
Dhar A. et al. Biopolymers. 2014 Jul;102(4):344-58.2014

Molecular specialization of breast vasculature: a breast-homing phage-displayed peptide binds to aminopeptidase P in breast vasculature.
Essler M. & Rouslahti E. Proc Natl Acad Sci U S A. 2002 Feb 19;99(4):2252-7.2002

Chemotherapy induces adaptive drug resistance and metastatic potentials via phenotypic CXCR4-expressing cell state transition in ovarian cancer
Lee H.H. et al. PLoS One. 2017 Feb 14;12(2):e0171044.2017

VHH characterization. Comparison of recombinant with chemically synthesized anti‐HER2 VHH
Lucie Hartmann, et al. Protein Science2019

Venoms and Toxins

Publications

Baltikinin: A New Myotropic Tryptophyllin-3 Peptide Isolated from the Skin Secretion of the Purple-Sided Leaf Frog, Phyllomedusa baltea.
Shi D. et al. Toxins, 8(7), 213.2016

AaeAP1 and AaeAP2: Novel Antimicrobial Peptides from the Venom of the Scorpion, Androctonus aeneas: Structural Characterisation, Molecular Cloning of Biosynthetic Precursor-Encoding cDNAs and Engineering of Analogues with Enhanced Antimicrobial and Anticancer Activities.
Du Q. et al. Toxins, 7(2), 219-237. 2015

Mambalgin-1 pain-relieving peptide: stepwise solid-phase synthesis, crystal structure and functional domain for acid-sensing ion channel 1a inhibition
Mourier G. et al. J. Biol. Chem. jbc.M115.702373. doi:10.1074/jbc.M115.702373 2015

Improved Detection of Botulinum Neurotoxin Serotype A by Endopep-MS through Peptide Substrate Modification
Wang D. et al. Analytical Biochemistry, 432(2), 115–123.2013

Comparison of the Catalytic Properties of the Botulinum Neurotoxin subtypes A1 and A5.
Wang D. et al. Biochimica et Biophysica Acta, 1834(12), 2722–2728.2013

High-throughput production of two disulphide-bridge toxins
Upert G. et al. Chem Commun (Camb). 2014 Aug 7;50(61):8408-11.2014

Kv1. 3 channel-blocking immunomodulatory peptides from parasitic worms: implications for autoimmune diseases
Chhabra S. et al. FASEB J. 2014

Vipericidins: a novel family of cathelicidin-related peptides from the venom gland of South American pit vipers.
Falcao C.B. et al. Amino Acids. 2014 Nov;46(11):2561-71.2014

δ-Conotoxins Synthesized Using an Acid-cleavable Solubility Tag Approach Reveal Key Structural Determinants for NaV Subtype Selectivity.
Peigneur S. et al. J Biol Chem. 2014 Dec 19; 289(51): 35341–35350.2014

New α-adrenergic property for synthetic MTβ and CM-3 three-finger fold toxins from black mamba.
Blanchet G. et al. Toxicon. 2013 Dec 1;75:160-7.2013

Peptidomic comparison and characterization of the major components of the venom of the giant ant Dinoponera quadriceps collected in four different areas of Brazil
Cologna C.T. et al. Journal of Proteomics Volume 94, 6 December 2013, Pages 413–422.2013

Inactivation of viruses infecting ectothermic animals by amphibian and piscine antimicrobial peptides.
Chinchar V.G. et al. Virology. 2004 Jun 1;323(2):268-75.2004

Expression, activation, and processing of the recombinant snake venom metalloproteinase, pro-atrolysin E.
Shimokawa K. et al. Arch Biochem Biophys. 1996 Nov 15;335(2):283-94.1996

Analgesic Effects of GpTx-1, PF-04856264 and CNV1014802 in a Mouse Model of NaV1.7-Mediated Pain
Deuis J.R. et al. Toxins 2016, 8(3), 78.2016

Enhanced detection of type C botulinum neurotoxin by the Endopep-MS assay through optimization of peptide substrates.
Wang D. et al. Bioorg Med Chem. 2015 Jul 1;23(13):3667-73.2015

‘Messy’ Processing of χ-conotoxin MrIA Generates Homologues with Reduced hNET Potency
Ziegman R. et al. Mar. Drugs 2019, 17(3), 165.2019

Novel conorfamides from Conus austini venom modulate both nicotinic acetylcholine receptors and acid-sensing ion channels
Jin A.-H. et al. Biochemical Pharmacology, In Press, Accepted Manuscript.2019

Insecticidal spider toxins are high affinity positive allosteric modulators of the nicotinic acetylcholine receptor
Chambers C. et al.  FEBS Lett. Accepted Author Manuscript. 2019

Repurposing the scorpion venom peptide VmCT1 into an active peptide against Gram-negative ESKAPE pathogens
Pedron C.N. et al. Bioorganic Chemistry,Available online 8 June 2019, 103038, In Press, Accepted Manuscript.2019

The effect of lysine substitutions in the biological activities of the scorpion venom peptide VmCT1
Pedron C.N. et al. European Journal of Pharmaceutical Sciences, Available online 7 June 2019. In Press, Accepted Manuscript.2019

Biomaterials

Drug delivery

General Research