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Pseudoproline Dipeptides

Pseudoproline dipeptides are useful building blocks developed by Mutter for preparing long or difficult peptides (Mutter M., et al. Pept. Res. 1995, 8, 145, Wöhr T., et al. J. Am. Chem. Soc. 1996, 118, 9218, White P, et al., J. Pept. Sci. 2004, 10, 18.) In the peptide chain, the amide bond between the pseudoproline dipeptide and the preceding amino acid preferentially adopts a cis configuration. This creates a kink in the peptide backbone that prevents self-association, β-sheet formation and peptide aggregation. By disrupting aggregation and β-sheet formation, incorporation of pseudoproline dipeptides into peptides used for fragment condensation reactions can markedly improve solubility. The tendency for pseudoprolines to form a kink in the peptide backbone promotes cyclization of linear peptides. Park and coworkers (Page K, et al. J. Pept. Sci. 2007, 13, 833.) found that incorporating a pseudoproline dipeptide accelerated the on resin cyclization of linear amylin (1-13). In addition, C-terminal pseudoprolines eliminate the risk of epimerization at the C-terminal during fragment coupling.

Pseudoproline dipeptides are powerful tools for enhancing the synthesis of cyclic peptides, long peptides and “difficult” peptides, often enabling the production of peptides that otherwise were impossible or impractical to synthesize.

Guidelines for Using Pseudoproline Dipeptides

1. If possible, insert pseudoprolines before hydrophobic regions.
2. There should be at least 2 amino acids between pseudoprolines or between pseudoprolines and prolines.
3. The optimum spacing is 5-6 amino acids between pseudoprolines or between pseudoprolines and prolines.

Showing 1–25 of 31 results

  • Fmoc-Ala-Ser(ψMe,Mepro)-OH [252554-78-2]
    Catalog # Product Name Unit Price Qty
    PPD001 Fmoc-Ala-Ser(ψMe,Mepro)-OH [252554-78-2]
    $45.00
  • Fmoc-Ala-Thr(ψMe,Mepro)-OH [252554-79-3]
    Catalog # Product Name Unit Price Qty
    PPD002 Fmoc-Ala-Thr(ψMe,Mepro)-OH [252554-79-3]
    $50.00
  • Fmoc-Asn(Trt)-Ser(ψMe,Mepro)-OH [920519-33-1]
    Catalog # Product Name Unit Price Qty
    PPD003 Fmoc-Asn(Trt)-Ser(ψMe,Mepro)-OH [920519-33-1]
    $55.00
  • Fmoc-Asn(Trt)-Thr(ψMe,Mepro)-OH   [957780-59-5]
    Catalog # Product Name Unit Price Qty
    PPD004 Fmoc-Asn(Trt)-Thr(ψMe,Mepro)-OH [957780-59-5]
    $50.00
  • Fmoc-Asp(OtBu)-Ser(ψMe,Mepro)-OH   [955048-92-7]
    Catalog # Product Name Unit Price Qty
    PPD005 Fmoc-Asp(OtBu)-Ser(ψMe,Mepro)-OH [955048-92-7]
    $55.00
  • Fmoc-Asp(OtBu)-Thr(ψMe,Mepro)-OH [920519-32-0]
    Catalog # Product Name Unit Price Qty
    PPD006 Fmoc-Asp(OtBu)-Thr(ψMe,Mepro)-OH [920519-32-0]
    $55.00
  • Fmoc-D-Val-D-Ser(psiMe,Me)pro-OH
    Catalog # Product Name Unit Price Qty
    PPD227 Fmoc-D-Val-D-Ser(psiMe,Me)pro-OH
    $200.00
  • Fmoc-Gln(Trt)-Ser(ψMe,Mepro)-OH
    Catalog # Product Name Unit Price Qty
    PPD007 Fmoc-Gln(Trt)-Ser(ψMe,Mepro)-OH
    $60.00
  • Fmoc-Gln(Trt)-Thr(ψMe,Mepro)-OH   [1572725-72-4]
    Catalog # Product Name Unit Price Qty
    PPD008 Fmoc-Gln(Trt)-Thr(ψMe,Mepro)-OH [1572725-72-4]
    $60.00
  • Fmoc-Glu(OtBu)-Ser(ψMe,Mepro)-OH [909115-33-9]
    Catalog # Product Name Unit Price Qty
    PPD009 Fmoc-Glu(OtBu)-Ser(ψMe,Mepro)-OH [909115-33-9]
    $60.00
  • Fmoc-Glu(OtBu)-Thr(ψMe,Mepro)-OH   [957780-56-2]
    Catalog # Product Name Unit Price Qty
    PPD010 Fmoc-Glu(OtBu)-Thr(ψMe,Mepro)-OH [957780-56-2]
    $55.00
  • Fmoc-Gly-Ser(ψMe, Mepro)-OH   [1095952-22-9]
    Catalog # Product Name Unit Price Qty
    PPD011 Fmoc-Gly-Ser(ψMe, Mepro)-OH [1095952-22-9]
    $45.00
  • Fmoc-Gly-Thr(ψMe,Mepro)-OH   [1262308-49-5]
    Catalog # Product Name Unit Price Qty
    PPD012 Fmoc-Gly-Thr(ψMe,Mepro)-OH [1262308-49-5]
    $45.00
  • Fmoc-Ile-Ser(ψMe,Mepro)-OH   [1147996-34-6]
    Catalog # Product Name Unit Price Qty
    PPD013 Fmoc-Ile-Ser(ψMe,Mepro)-OH [1147996-34-6]
    $50.00
  • Fmoc-Ile-Thr(ψMe,Mepro)-OH   [957780-52-8]
    Catalog # Product Name Unit Price Qty
    PPD014 Fmoc-Ile-Thr(ψMe,Mepro)-OH [957780-52-8]
    $45.00
  • Fmoc-Leu-Ser(ψMe,Mepro)-OH  [339531-50-9]
    Catalog # Product Name Unit Price Qty
    PPD015 Fmoc-Leu-Ser(ψMe,Mepro)-OH [339531-50-9]
    $50.00
  • Fmoc-Leu-Thr(ψMe,Mepro)-OH [955048-89-2]
    Catalog # Product Name Unit Price Qty
    PPD016 Fmoc-Leu-Thr(ψMe,Mepro)-OH [955048-89-2]
    $45.00
  • Fmoc-Lys(Boc)-Ser(ψMe,Mepro)-OH   [957780-54-0]
    Catalog # Product Name Unit Price Qty
    PPD017 Fmoc-Lys(Boc)-Ser(ψMe,Mepro)-OH [957780-54-0]
    $55.00
  • Fmoc-Lys(Boc)-Thr(ψMe,Mepro)-OH [911838-56-7]
    Catalog # Product Name Unit Price Qty
    PPD018 Fmoc-Lys(Boc)-Thr(ψMe,Mepro)-OH [911838-56-7]
    $55.00
  • Fmoc-Phe-Ser(ψMe,Mepro)-OH [878797-01-4]
    Catalog # Product Name Unit Price Qty
    PPD019 Fmoc-Phe-Ser(ψMe,Mepro)-OH [878797-01-4]
    $55.00
  • Fmoc-Phe-Thr(ψMe,Mepro)-OH   [1196703-48-6]
    Catalog # Product Name Unit Price Qty
    PPD020 Fmoc-Phe-Thr(ψMe,Mepro)-OH [1196703-48-6]
    $55.00
  • Fmoc-Ser(tBu)-Ser(ψMe,Mepro)-OH   [1000164-43-1]
    Catalog # Product Name Unit Price Qty
    PPD021 Fmoc-Ser(tBu)-Ser(ψMe,Mepro)-OH [1000164-43-1]
    $60.00
  • Fmoc-Ser(tBu)-Thr(ψMe,Mepro)-OH   [1266350-99-5]
    Catalog # Product Name Unit Price Qty
    PPD022 Fmoc-Ser(tBu)-Thr(ψMe,Mepro)-OH [1266350-99-5]
    $55.00
  • Fmoc-Thr(tBu)-Ser(ΨMe,Mepro)-OH   [1425938-63-1]
    Catalog # Product Name Unit Price Qty
    PPD029 Fmoc-Thr(tBu)-Ser(ψMe,Mepro)-OH [1425938-63-1]
    $55.00
  • Fmoc-Thr(tBu)-Thr(psi Me,Me pro)-OH   [1676104-73-6]
    Catalog # Product Name Unit Price Qty
    PPD030 Fmoc-Thr(tBu)-Thr(ψMe,Mepro)-OH [1676104-73-6]
    $55.00