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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). Incorporation of pseudoproline dipeptides in the linear peptide promoted cyclization by ring closing metathesis (N. Schmiedeburg, H. Kessler, Org. Lett., 2002, 4(1), 59-62). 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 32 results

  • Fmoc-Ala-Ser(ψMe,Mepro)-OH [252554-78-2]
    Catalog #Product NameUnitPriceQty
    PPD001Fmoc-Ala-Ser(ψMe,Mepro)-OH [252554-78-2]
    $65.00
  • Fmoc-Ala-Thr(ψMe,Mepro)-OH [252554-79-3]
    Catalog #Product NameUnitPriceQty
    PPD002Fmoc-Ala-Thr(ψMe,Mepro)-OH [252554-79-3]
    $65.00
  • Fmoc-Asn(Trt)-Ser(ψMe,Mepro)-OH [920519-33-1]
    Catalog #Product NameUnitPriceQty
    PPD003Fmoc-Asn(Trt)-Ser(ψMe,Mepro)-OH [920519-33-1]
    $65.00
  • Fmoc-Asn(Trt)-Thr(ψMe,Mepro)-OH [957780-59-5]
    Catalog #Product NameUnitPriceQty
    PPD004Fmoc-Asn(Trt)-Thr(ψMe,Mepro)-OH [957780-59-5]
    $75.00
  • Fmoc-Asp(OtBu)-Ser(ψMe,Mepro)-OH [955048-92-7]
    Catalog #Product NameUnitPriceQty
    PPD005Fmoc-Asp(OtBu)-Ser(ψMe,Mepro)-OH [955048-92-7]
    $75.00
  • Fmoc-Asp(OtBu)-Thr(ψMe,Mepro)-OH [920519-32-0]
    Catalog #Product NameUnitPriceQty
    PPD006Fmoc-Asp(OtBu)-Thr(ψMe,Mepro)-OH [920519-32-0]
    $75.00
  • Fmoc-D-Val-D-Ser(psiMe,Me)pro-OH
    Catalog #Product NameUnitPriceQty
    PPD227Fmoc-D-Val-D-Ser(psiMe,Me)pro-OH
    $200.00
  • Fmoc-Gln(Trt)-Ser(ψMe,Mepro)-OH
    Catalog #Product NameUnitPriceQty
    PPD007Fmoc-Gln(Trt)-Ser(ψMe,Mepro)-OH
    $75.00
  • Fmoc-Gln(Trt)-Thr(ψMe,Mepro)-OH [1572725-72-4]
    Catalog #Product NameUnitPriceQty
    PPD008Fmoc-Gln(Trt)-Thr(ψMe,Mepro)-OH [1572725-72-4]
    $65.00
  • Fmoc-Glu(OtBu)-Ser(ψMe,Mepro)-OH [909115-33-9]
    Catalog #Product NameUnitPriceQty
    PPD009Fmoc-Glu(OtBu)-Ser(ψMe,Mepro)-OH [909115-33-9]
    $75.00
  • Fmoc-Glu(OtBu)-Thr(ψMe,Mepro)-OH [957780-56-2]
    Catalog #Product NameUnitPriceQty
    PPD010Fmoc-Glu(OtBu)-Thr(ψMe,Mepro)-OH [957780-56-2]
    $75.00
  • Fmoc-Gly-Ser(ψMe, Mepro)-OH [1095952-22-9]
    Catalog #Product NameUnitPriceQty
    PPD011Fmoc-Gly-Ser(ψMe, Mepro)-OH [1095952-22-9]
    $75.00
  • Fmoc-Gly-Thr(ψMe,Mepro)-OH [1262308-49-5]
    Catalog #Product NameUnitPriceQty
    PPD012Fmoc-Gly-Thr(ψMe,Mepro)-OH [1262308-49-5]
    $75.00
  • Fmoc-Ile-Ser(ψMe,Mepro)-OH [1147996-34-6]
    Catalog #Product NameUnitPriceQty
    PPD013Fmoc-Ile-Ser(ψMe,Mepro)-OH [1147996-34-6]
    $80.00
  • Fmoc-Ile-Thr(ψMe,Mepro)-OH [957780-52-8]
    Catalog #Product NameUnitPriceQty
    PPD014Fmoc-Ile-Thr(ψMe,Mepro)-OH [957780-52-8]
    $65.00
  • Fmoc-Leu-Ser(ψMe,Mepro)-OH [339531-50-9]
    Catalog #Product NameUnitPriceQty
    PPD015Fmoc-Leu-Ser(ψMe,Mepro)-OH [339531-50-9]
    $80.00
  • Fmoc-Leu-Thr(ψMe,Mepro)-OH [955048-89-2]
    Catalog #Product NameUnitPriceQty
    PPD016Fmoc-Leu-Thr(ψMe,Mepro)-OH [955048-89-2]
    $80.00
  • Fmoc-Lys(Boc)-Ser(ψMe,Mepro)-OH [957780-54-0]
    Catalog #Product NameUnitPriceQty
    PPD017Fmoc-Lys(Boc)-Ser(ψMe,Mepro)-OH [957780-54-0]
    $80.00
  • Fmoc-Lys(Boc)-Thr(ψMe,Mepro)-OH [911838-56-7]
    Catalog #Product NameUnitPriceQty
    PPD018Fmoc-Lys(Boc)-Thr(ψMe,Mepro)-OH [911838-56-7]
    $75.00
  • Catalog #Product NameUnitPriceQty
    PPD045Fmoc-Met-Ser[psi(me,Me)pro]-OH
    $400.00
  • Fmoc-Phe-Ser(ψMe,Mepro)-OH [878797-01-4]
    Catalog #Product NameUnitPriceQty
    PPD019Fmoc-Phe-Ser(ψMe,Mepro)-OH [878797-01-4]
    $65.00
  • Fmoc-Phe-Thr(ψMe,Mepro)-OH [1196703-48-6]
    Catalog #Product NameUnitPriceQty
    PPD020Fmoc-Phe-Thr(ψMe,Mepro)-OH [1196703-48-6]
    $80.00
  • Fmoc-Ser(tBu)-Ser(ψMe,Mepro)-OH [1000164-43-1]
    Catalog #Product NameUnitPriceQty
    PPD021Fmoc-Ser(tBu)-Ser(ψMe,Mepro)-OH [1000164-43-1]
    $80.00
  • Fmoc-Ser(tBu)-Thr(ψMe,Mepro)-OH [1266350-99-5]
    Catalog #Product NameUnitPriceQty
    PPD022Fmoc-Ser(tBu)-Thr(ψMe,Mepro)-OH [1266350-99-5]
    $55.00
  • Fmoc-Thr(tBu)-Ser(ΨMe,Mepro)-OH [1425938-63-1]
    Catalog #Product NameUnitPriceQty
    PPD029Fmoc-Thr(tBu)-Ser(ψMe,Mepro)-OH [1425938-63-1]
    $75.00