α-Azido Acids in Solid-Phase Peptide Synthesis: Compatibility with Fmoc Chemistry and an Alternative Approach to the Solid Phase Synthesis of Daptomycin Analogs

2016 ◽  
Vol 81 (6) ◽  
pp. 2624-2628 ◽  
Author(s):  
Chuda Raj Lohani ◽  
Benjamin Rasera ◽  
Bradley Scott ◽  
Michael Palmer ◽  
Scott D. Taylor
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Phase Synthesis ◽  
Fmoc Chemistry ◽  
Alternative Approach

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.

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.

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

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.

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>

The Boc/Solid Phase Synthesis of Glu-Abu(P)-Leu

1992 ◽  
Vol 45 (10) ◽  
pp. 1765 ◽  
Author(s):  
JW Perich ◽  
EC Reynolds
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hydrogen Bromide ◽  
Solid Phase Peptide Synthesis ◽  
Polymer Support ◽  
Methyl Groups ◽  
Phase Synthesis

The synthesis of the 4-phosphono-2-aminobutanoyl-containing tripeptide , H- Glu -Abu(P)- Leu-OH.CF3C02H was accomplished by the use of Boc-Abu(PO3Me2)-OH in Boc /solid phase peptide synthesis. Peptide synthesis was performed by using Boc-Leu-polystyrene as the polymer support with the peptide assembled by the use of 1H-benzotriazol-1-yloxytris(pyrro1idin-1-yl) phosphonium hexafluorophosphate ( PyBOPR ) for the coupling of Boc amino acids and 50% CF3C02H/CH2C12 for cleavage of the Boc group from the Boc -peptide after each coupling cycle. The protected peptide was cleaved from the polymer support by hydrogen bromide in trifluoroacetic acid and final cleavage of the methyl groups from Glu-Abu(PO2Me2)-Leu was effected by silylitic treatment with 30% bromotrimethylsilane in acetonitrile.

Post-synthetically Ligated Ribozymes:  An Alternative Approach to Iterative Solid-Phase Synthesis

1997 ◽  
Vol 8 (2) ◽  
pp. 204-212 ◽  
Author(s):  
Laurent Bellon ◽  
Christopher T. Workman ◽  
Thale C. Jarvis ◽  
Francine E. Wincott
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Alternative Approach
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