Optimized Fmoc solid‐phase synthesis of the cysteine‐rich peptide linaclotide

@article{GngoraBentez2011OptimizedFS,
  title={Optimized Fmoc solid‐phase synthesis of the cysteine‐rich peptide linaclotide},
  author={Miriam G{\'o}ngora-Ben{\'i}tez and J. Tulla-Puche and Marta Parad{\'i}s-Bas and O. Werbitzky and M. Giraud and F. Albericio},
  journal={Peptide Science},
  year={2011},
  volume={96}
}
Linaclotide, a small 14‐mer peptide highly rich in cysteines, is currently in phase III clinical trials for the treatment of gastrointestinal disorders. The challenge in the assembly of linaclotide consists of achieving the correct and clean folding of its three disulfide bridges. For this purpose, a number of regioselective, semiregioselective, and random strategies have been studied. In addition to selecting distinct protecting groups for the thiol function, their position in the sequence… Expand
View on Wiley
pdf.xuebalib.com:1262
37 Citations
Highly Influential Citations
1
Background Citations
3
Methods Citations
4

37 Citations

Citation Type

Citation Type

Diaminodiacid Bridges to Improve Folding and Tune the Bioactivity of Disulfide-Rich Peptides.
  • 41
Stepwise Construction of Disulfides in Peptides
A rapid and efficient method for the synthesis of selectively S-Trt or S-Mmt protected Cys-containing peptides
  • 5
  • Highly Influenced
Orthogonal Cysteine-Penicillamine Disulfide Pairing for Directing the Oxidative Folding of Peptides.
  • 26
Total synthesis of human hepcidin through regioselective disulfide-bond formation by using the safety-catch cysteine protecting group 4,4'-dimethylsulfinylbenzhydryl.
  • 29
Of Thiols and Disulfides: Methods for Chemoselective Formation of Asymmetric Disulfides in Synthetic Peptides and Polymers.
  • 11
Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in Fmoc solid phase synthesis.
  • 32
  • PDF
Chemical synthesis and structural analysis of guanylate cyclase C agonist linaclotide
  • 7
Synthesis of Four-Disulfide Insulin Analogs via Sequential Disulfide Bond Formation.
  • 17
Raising the Bar On-Bead: Efficient On-Resin Synthesis of α-Conotoxin LvIA.
  • 2
...
1
2
3
4
...

References

SHOWING 1-10 OF 27 REFERENCES
On the use of s-t-butylsulphenyl group for protection of cysteine in solid-phase peptide synthesis using fmoc-amino acids
  • 57
The chemistry and biology of cyclotides.
  • 53
Regioselective formation, using orthogonal cysteine protection, of an alpha-conotoxin dimer peptide containing four disulfide bonds.
  • 41
Occurrence and Minimization of Cysteine Racemization during Stepwise Solid-Phase Peptide Synthesis(1)(,)(2).
  • 165
Cyclization of disulfide-containing peptides in solid-phase synthesis.
  • 69
Synthesis of α-conotoxin SI, a bicyclic tridecapeptide amide with two disulfide bridges : illustration of novel protection schemes and oxidation strategies
  • 45
Characterization and structural role of disulfide bonds in a highly knotted thionin from Pyrularia pubera
  • 10
Mode of disulfide bond formation of a heat‐stable enterotoxin (STh) produced by a human strain of enterotoxigenic Escherichia coli
  • 58
The synthesis of cystine peptides by iodine oxidation of s trityl cysteine and s acetamidomethyl cysteine peptides
  • 203
Synthesis of palmitoyl‐thioester T‐cell epitopes of myelin proteolipid protein (PLP). Comparison of two thiol protecting groups (StBu and Mmt) for on‐resin acylation
  • B. Denis, É. Trifilieff
  • Chemistry, Medicine
  • Journal of peptide science : an official publication of the European Peptide Society
  • 2000
  • 30
...
1
2
3
...