Solid phase synthesis of α-amino squaric acid-containing peptides

RSC Advances ◽  
2014 ◽  
Vol 4 (92) ◽  
pp. 50639-50643 ◽  
Author(s):  
Kentaro Maeda ◽  
Yu-ichi Kiniwa ◽  
Yasufumi Ohfune ◽  
Shinichi Ishiguro ◽  
Koichi Suzuki ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
New Method ◽  
Squaric Acid ◽  
Protecting Group ◽  
Phase Synthesis ◽  
Group Strategy ◽  
Fmoc Protecting Group

A new method has been developed for the synthesis of 3-(1-aminoalkyl)-4-hydroxycyclobut-3-ene-1,2-dione [(α-amino squaric acid (α-Asq)]-containing peptides using solid phase peptide synthesis according to an Fmoc protecting group strategy.

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.

Solid-phase synthesis of RNA via a silyl-protecting-group strategy

2010 ◽  
Vol 110 (9) ◽  
pp. 378-383 ◽  
Author(s):  
C. M. Dreef-Tromp ◽  
E. M. A. van Dam ◽  
H. van den Elst ◽  
J. E. van den Boogaart ◽  
G. A. van der Marel ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Protecting Group ◽  
Phase Synthesis ◽  
Group Strategy

scholarly journals Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 4004 ◽  
Author(s):  
Ashish Kumar ◽  
Anamika Sharma ◽  
Beatriz G. de la Torre ◽  
Fernando Albericio
Keyword(s):  
Peptide Synthesis ◽  
Ring Opening ◽  
Solid Phase ◽  
Theoretical Calculations ◽  
Solid Phase Peptide Synthesis ◽  
Time Dependent ◽  
Green Solvent ◽  
Protecting Group ◽  
Fmoc Protecting Group

GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitoring using NMR. The results, corroborated by theoretical calculations, indicate that a solution of piperidines in GVL should be prepared daily for a better Fmoc removal.

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.

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.

Sign in / Sign up

Export Citation Format

Share Document