Synthesis of Asparagusic Acid Modified Lysine and its Application in Solid-Phase Synthesis of Peptides with Enhanced Cellular Uptake

Synlett ◽  
2017 ◽  
Vol 29 (10) ◽  
pp. 1289-1292 ◽  
Author(s):  
Pablo Rivera-Fuentes ◽  
Alina Tirla ◽  
Moritz Hansen
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Cellular Uptake ◽  
Building Block ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Live Cells ◽  
Phase Synthesis ◽  
Scalable Synthesis

Cyclic disulfides, such as asparagusic acid, enhance the uptake of a variety of cargoes into live cells. Here, we report a robust and scalable synthesis of an asparagusic acid modified lysine. This amino acid can be used in solid-phase peptide synthesis. We confirmed that incorporation of this building block into the sequence of a peptide increases its cellular uptake substantially.

scholarly journals Efficient Synthesis of Peptides with 4-Methylpiperidine as Fmoc Removal Reagent by Solid Phase Synthesis

2017 ◽  
Vol 58 (4) ◽  
Author(s):  
Javier Eduardo García Castañeda ◽  
Cristian Francisco Vergel Galeano ◽  
Zuly Jenny Rivera Monroy ◽  
Javier Eduardo Rosas Pérez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Synthetic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Amino Group ◽  
Efficient Synthesis ◽  
Phase Synthesis

<p>Solid phase peptide synthesis using the Fmoc/<em>t</em>-Bu strategy (SPPS-Fmoc/tBu) is the most widely used methodology for obtaining synthetic peptides. In this paper, we evaluate the viability of using 4-methylpiperidine as a reagent for deprotection of the amino acid alpha amino group in SPPS-Fmoc/tBu. For this purpose, the peptide (RRWQWRMKKLG) was simultaneously synthesized using 4-methylpiperidine or piperidine for Fmoc removal reagent. The obtained products had similar purities and yields. Finally, 21 peptides were synthesized using 4-methylpiperidine. Our results suggest that is possible to obtain synthetic peptides efficiently by the strategy SPPS-Fmoc/tBu when 4-methylpiperidine was used as reagent to remove Fmoc groups N-alpha protected amino acids.</p>

Synthesis of Casein-Related Peptides and Phosphopeptides. II. The Solid-Phase Synthesis of the Nonphosphorylated Octapeptide Corresponding to Region-14-21 of Bovine β-Casein-A2

1987 ◽  
Vol 40 (8) ◽  
pp. 1389 ◽  
Author(s):  
JW Perich ◽  
NJ Langford ◽  
RB Johns
Keyword(s):  
Mass Spectrometry ◽  
Structural Analysis ◽  
Peptide Synthesis ◽  
Fast Atom Bombardment ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Phase Synthesis

The octapeptide CF3C02-. + H2-Glu-Ser-Leu-Ser-Ser-Ser-Glu-Glu-OH (1) was synthesized by the Boc-mode of solid-phase peptide synthesis and hydrogenolytic cleavage of the assembled peptide from the resin support. The 13C n.m.r. spectrum of the octapeptide is presented along with its structural analysis by fast-atom bombardment (f.a.b.) mass spectrometry.

scholarly journals The synthesis of an EDTA-like chelating peptidomimetic building block suitable for solid-phase peptide synthesis

2017 ◽  
Vol 53 (17) ◽  
pp. 2634-2636 ◽  
Author(s):  
Jan Spengler ◽  
Michael Barker ◽  
Constanze Schelhorn ◽  
Jesús García ◽  
Maria J. Macias ◽  
...  
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Building Block ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis

A novo trifunctional EDTA-like peptidomimetic amino acid is described.

scholarly journals Development of the Schedule for Multiple Parallel “Difficult” Peptide Synthesis on Pins

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Ekaterina F. Kolesanova ◽  
Maxim A. Sanzhakov ◽  
Oleg N. Kharybin
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Standard Procedure ◽  
Bromophenol Blue ◽  
Virus Envelope ◽  
Phase Synthesis ◽  
Terminal Amino ◽  
Difficult Peptide Synthesis

Unified schedule for multiple parallel solid-phase synthesis of so-called “difficult” peptides on polypropylene pins was developed. Increase in the efficiency of 9-fluorenyl(methoxycarbonyl) N-terminal amino-protecting group removal was shown to have a greater influence on the accuracy of the “difficult” peptide synthesis than the use of more efficient amino acid coupling reagents such as aminium salts. Hence the unified schedule for multiple parallel solid-phase synthesis of “difficult” peptides included the procedure for N-terminal amino group deprotection modified by applying a more efficient reagent for the deprotection and the standard procedure of amino acid coupling by carbodiimide method with an additional coupling using aminium salts, if necessary. Amino acid coupling with the help of carbodiimide allows to follow the completeness of the coupling via the bromophenol blue indication, thus providing the accuracy of the synthesis and preventing an overexpenditure of expensive reagents. About 100 biotinylated hepatitis C virus envelope protein fragments, most of which represented “difficult” peptides, were successfully obtained by synthesis on pins with the help of the developed unified schedule.

Diaminodiacid-based solid-phase synthesis of all-hydrocarbon stapled α-helical peptides

2015 ◽  
Vol 13 (22) ◽  
pp. 6286-6290 ◽  
Author(s):  
Feng-Liang Wang ◽  
Ye Guo ◽  
Si-Jian Li ◽  
Qing-Xiang Guo ◽  
Jing Shi ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Helical Peptides ◽  
Phase Synthesis

An alternative stapling strategy is described herein using Fmoc-solid phase peptide synthesis (SPSS) that employed pre-prepared diaminodiacid building blocks to introduce all-hydrocarbon staples into peptides by on-resin cyclization.

Solid-Phase Synthesis of Peptides via a,β-Unsaturated Amino Acids. Incorporation of the Amide Gronp in encZo-Positions

1981 ◽  
Vol 36 (10) ◽  
pp. 1345-1348 ◽  
Author(s):  
Kosaku Nöda ◽  
Erhard Gross
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Phase Synthesis ◽  
Unsaturated Amino Acids ◽  
Model Peptides

Abstract Dehydroalanine is introduced as pseudoprotecting group for the to-amide function of Asn and Gin in solid-phase peptide synthesis. Using Boc-X(Dha-NHMe)-OH (X = Asp or Glu), the model peptides, L-Leu-L-Asn-Gly-NH2 and L-Leu-Lr-Gln-Gly-NH2, were synthesized

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