+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

Investigation of the automated solid-phase synthesis of a 38mer peptide with difficult sequence pattern under different synthesis strategies

Investigation of the automated solid-phase synthesis of a 38mer peptide with difficult sequence pattern under different synthesis strategies

Amino Acids 47(4): 787-794

Difficult peptides are a constant challenge in solid-phase peptide synthesis. In particular, hydroxyl amino acids such as serine can cause severe breakdowns in coupling yields even several amino acids after the insertion of the critical amino acid. This paper investigates several methods of improving synthesis yields of difficult peptides including the use of different resins, activators and the incorporation of a structure-breaking pseudoproline dipeptide building block both alone and in combination with each other.

(PDF emailed within 0-6 h: $19.90)

Accession: 058159168

Download citation: RISBibTeXText

PMID: 25595601

DOI: 10.1007/s00726-014-1909-6

Related references

Convergent solid-phase peptide synthesis performed in a CHCl3-phenol mixed solvent: Synthesis of amyloid beta-peptides as examples with a difficult sequence. International Journal of Peptide Research and Therapeutics 13(1-2): 119-128, 2007

Amyloid-beta as a "difficult sequence" in solid phase peptide synthesis. Protein and Peptide Letters 11(4): 377-384, 2004

An improved solid phase synthesis of a difficult sequence peptide using hexafluoro 2 propanol. International Journal of Peptide & Protein Research 36(2): 193-196, 1990

High-yield, solid-phase synthesis of humanin, an Alzheimer's disease associated, novel 24-mer peptide which contains a difficult sequence. Journal of Peptide Science 10(10): 631-635, 2004

Application of a partially automated solid phase peptide synthesis apparatus to the synthesis of a protected peptide fragment of cytochrome c. Analytical Biochemistry 85(2): 367-376, 1978

Aqueous microwave-assisted solid-phase peptide synthesis using Fmoc strategy: in-water synthesis of "difficult sequences". Protein and Peptide Letters 19(11): 1231-1236, 2013

Synthesis of a 6,6-spiroketal amino acid and its incorporation into a peptide turn sequence using solid-phase peptide synthesis. Chemistry 19(12): 3807-3811, 2013

Comparative investigation of the cleavage step in the synthesis of model peptide resins: implications for Nalpha-9-fluorenylmethyloxycarbonyl-solid phase peptide synthesis. Chemical & Pharmaceutical Bulletin 55(3): 468-470, 2007

Solid phase peptide synthesis part 1 a mild method of solid phase peptide synthesis employing an enamine nitrogen protecting group and a benzhydryl resin as a solid support. Tetrahedron Letters 40: 3505-3508, 1969

Convergent solid-phase peptide synthesis XI Synthesis and purification of protected peptide segments spanning the entire sequence of the uteroglobin monomer using the photolabile Nbb-resin. Tetrahedron 49(44): 10069-10078, 1993

Peptide synthesis part 13. feedback control in solid phase synthesis use of fluorenylmethoxycarbonyl amino acid 3 4 dihydro 4 oxo 1 2 3 benzotriazin 3 yl esters in a fully automated system. Journal of the Chemical Society Perkin Transactions I (10): 2895-2901, 1988

Prediction of difficult sequences in solid phase peptide synthesis. Journal of the American Chemical Society 112(16): 6039-6046, 1990

Optimization of solid-phase synthesis of difficult peptide sequences. 2007

Overview of solid phase synthesis of "difficult peptide" sequences. Current Protocols in Protein Science Chapter 18: Unit 18.8-Unit 18.8, 2008

A facile method for the synthesis of benzyl esters using benzyl bromide or iodide and its application to solid phase and conventional peptide synthesis; attempted sterical selection in solid phase synthesis. Tetrahedron Letters: 6323-6326, 1968