scholarly journals A novel PEG-based solid support enables the synthesis of >50 amino-acid peptide thioesters and the total synthesis of a functional SUMO-1 peptide conjugate

2014 ◽  
Vol 5 (5) ◽  
pp. 2017-2022 ◽  
Author(s):  
Emmanuelle Boll ◽  
Hervé Drobecq ◽  
Nathalie Ollivier ◽  
Laurent Raibaut ◽  
Rémi Desmet ◽  
...  
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Solid Support ◽  
Amino Acid Peptide ◽  
Peptide Thioester ◽  
Large Peptide ◽  
Peptide Thioesters

Bis(2-sulfanylethyl)amino PEG resin gives access to large peptide thioester segments and to functional SUMO-1 conjugates.

scholarly journals Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation

2017 ◽  
Vol 8 (1) ◽  
pp. 117-123 ◽  
Author(s):  
Hader E. Elashal ◽  
Yonnette E. Sim ◽  
Monika Raj
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Solid Support ◽  
Native Chemical Ligation ◽  
Selective Activation ◽  
Chemical Ligation ◽  
Peptide Thioester ◽  
Peptide Thioesters

Fmoc solid phase peptide synthesis of peptide thioesters by displacement of the cyclic urethane moiety obtained by the selective activation of C-terminal serine.

scholarly journals Insights into the Mechanism and Catalysis of Peptide Thioester Synthesis by Alkylselenols Provide a New Tool for Chemical Protein Synthesis

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1386
Author(s):  
Florent Kerdraon ◽  
Gemma Bogard ◽  
Benoît Snella ◽  
Hervé Drobecq ◽  
Muriel Pichavant ◽  
...  
Keyword(s):  
Protein Synthesis ◽  
Total Synthesis ◽  
Adaptive Immunity ◽  
Biologically Active ◽  
Acidic Ph ◽  
Innate And Adaptive Immunity ◽  
Chemotactic Protein ◽  
Chemical Protein Synthesis ◽  
Peptide Thioester ◽  
Peptide Thioesters

While thiol-based catalysts are widely employed for chemical protein synthesis relying on peptide thioester chemistry, this is less true for selenol-based catalysts whose development is in its infancy. In this study, we compared different selenols derived from the selenocysteamine scaffold for their capacity to promote thiol–thioester exchanges in water at mildly acidic pH and the production of peptide thioesters from bis(2-sulfanylethyl)amido (SEA) peptides. The usefulness of a selected selenol compound is illustrated by the total synthesis of a biologically active human chemotactic protein, which plays an important role in innate and adaptive immunity.

Endohexosaminidase-catalyzed synthesis of glycopeptides and proteins

2013 ◽  
Vol 85 (9) ◽  
pp. 1847-1863 ◽  
Author(s):  
Antony J. Fairbanks
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Natural Sources ◽  
Glcnac Residue ◽  
Amino Acid Peptide ◽  
Ready Access ◽  
Synthetic Application

The synthetic application of endohexosaminidase enzymes (e.g., Endo A, Endo M, Endo D) promises to allow ready access to a wide variety of defined homogeneous glycoproteins and glycopeptides. The use ofN-glycan oligosaccharides that are activated at the reducing terminus as oxazolines allows their high-yielding attachment to almost any amino acid, peptide, or protein that contains a GlcNAc residue as an acceptor. A wide variety of oxazoline donors are readily available, either by total synthesis or by isolation of the corresponding oligosaccharide from natural sources and then conversion to the oxazoline in water. The synthetic potential of the enzymes is particularly augmented by the production of mutant glycosynthases, the use of which allows the synthesis of a wide variety of glycopeptides and glycoproteins bearing defined homogeneousN-glycan structures.

scholarly journals Insights into the Mechanism and Catalysis of Peptide Thioester Synthesis by Alkylselenols Provide a New Tool for Chemical Protein Synthesis

2021 ◽  
Author(s):  
Florent kerdraon ◽  
Gemma Bogard ◽  
Benoît Snella ◽  
Hervé Drobecq ◽  
Muriel Pichavant ◽  
...  
Keyword(s):  
Protein Synthesis ◽  
Total Synthesis ◽  
Adaptive Immunity ◽  
Biologically Active ◽  
Acidic Ph ◽  
Innate And Adaptive Immunity ◽  
Chemotactic Protein ◽  
Chemical Protein Synthesis ◽  
Peptide Thioester ◽  
Peptide Thioesters

While thiol-based catalysts are widely employed for chemical protein synthesis relying on peptide thioester chemistry, this is less true for selenol-based catalysts whose development is in its infancy. In this study, we compared different selenols derived from the selenocysteamine scaffold for their capacity to promote thiol-thioester exchanges in water at mildly acidic pH and the production of peptide thioesters from bis(2-sulfanylethyl)amido (SEA) peptides. The usefulness of a selected selenol compound is illustrated by the total synthesis of a biologically active human chemotactic protein, which plays an important role in innate and adaptive immunity<br>

scholarly journals Insights into the Mechanism and Catalysis of Peptide Thioester Synthesis by Alkylselenols Provide a New Tool for Chemical Protein Synthesis

2021 ◽  
Author(s):  
Florent kerdraon ◽  
Gemma Bogard ◽  
Benoît Snella ◽  
Hervé Drobecq ◽  
Muriel Pichavant ◽  
...  
Keyword(s):  
Protein Synthesis ◽  
Total Synthesis ◽  
Adaptive Immunity ◽  
Biologically Active ◽  
Acidic Ph ◽  
Innate And Adaptive Immunity ◽  
Chemotactic Protein ◽  
Chemical Protein Synthesis ◽  
Peptide Thioester ◽  
Peptide Thioesters

While thiol-based catalysts are widely employed for chemical protein synthesis relying on peptide thioester chemistry, this is less true for selenol-based catalysts whose development is in its infancy. In this study, we compared different selenols derived from the selenocysteamine scaffold for their capacity to promote thiol-thioester exchanges in water at mildly acidic pH and the production of peptide thioesters from bis(2-sulfanylethyl)amido (SEA) peptides. The usefulness of a selected selenol compound is illustrated by the total synthesis of a biologically active human chemotactic protein, which plays an important role in innate and adaptive immunity<br>

Immunoelectron microscope detection of C-type natriuretic peptide in normal human atrial tissue

1993 ◽  
Vol 51 ◽  
pp. 388-389
Author(s):  
Chi-Ming Wei ◽  
Margaret Hukee ◽  
Christopher G.A. McGregor ◽  
John C. Burnett
Keyword(s):  
Amino Acid ◽  
Natriuretic Peptide ◽  
Vascular Tone ◽  
Cardiac Tissue ◽  
Ring Structure ◽  
Terminal Amino Acid ◽  
Amino Acid Peptide ◽  
Normal Human ◽  
Terminal Amino ◽  
The Brain

C-type natriuretic peptide (CNP) is a newly identified peptide that is structurally related to atrial (ANP) and brain natriuretic peptide (BNP). CNP exists as a 22-amino acid peptide and like ANP and BNP has a 17-amino acid ring formed by a disulfide bond. Unlike these two previously identified cardiac peptides, CNP lacks the COOH-terminal amino acid extension from the ring structure. ANP, BNP and CNP decrease cardiac preload, but unlike ANP and BNP, CNP is not natriuretic. While ANP and BNP have been localized to the heart, recent investigations have failed to detect CNP mRNA in the myocardium although small concentrations of CNP are detectable in the porcine myocardium. While originally localized to the brain, recent investigations have localized CNP to endothelial cells consistent with a paracrine role for CNP in the control of vascular tone. While CNP has been detected in cardiac tissue by radioimmunoassay, no studies have demonstrated CNP localization in normal human heart by immunoelectron microscopy.

scholarly journals A C-peptide complex with albumin and Zn2+ increases measurable GLUT1 levels in membranes of human red blood cells

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
M. Geiger ◽  
T. Janes ◽  
H. Keshavarz ◽  
S. Summers ◽  
C. Pinger ◽  
...  
Keyword(s):  
Type 1 Diabetes ◽  
Amino Acid ◽  
Blood Cells ◽  
Glucose Transporter ◽  
Peptide Binding ◽  
C Peptide ◽  
Amino Acid Peptide ◽  
Human Red Blood Cells

Abstract People with type 1 diabetes (T1D) require exogenous administration of insulin, which stimulates the translocation of the GLUT4 glucose transporter to cell membranes. However, most bloodstream cells contain GLUT1 and are not directly affected by insulin. Here, we report that C-peptide, the 31-amino acid peptide secreted in equal amounts with insulin in vivo, is part of a 3-component complex that affects red blood cell (RBC) membranes. Multiple techniques were used to demonstrate saturable and specific C-peptide binding to RBCs when delivered as part of a complex with albumin. Importantly, when the complex also included Zn2+, a significant increase in cell membrane GLUT1 was measured, thus providing a cellular effect similar to insulin, but on a transporter on which insulin has no effect.

Ternary metal/nucleobase (oligonucleotide)/amino acid (peptide) complexes

1995 ◽  
Vol 59 (2-3) ◽  
pp. 147 ◽  
Author(s):  
H. Witkowski ◽  
I. Rombeck ◽  
T. Wienkötter ◽  
S. Höhmann ◽  
A. Erxleben ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Peptide ◽  
Ternary Metal ◽  
Peptide Complexes
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