Modifications: Special Amino Acids

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Modifications: special amino acids

LifeTein offers special amino acids and modifications, including N-methyl amino acids, unnatural amino acids, acetyl-lysine, beta-alanine, aminobenzoic acid, amidation, acetylation, Abu, citrulline, Acm, dimethyl-lysine, hydroxy-proline (Hyp), methyl-lysine, mercaptopropionic acid, nitro-tyrosine, norleucine (Nle), pyro-glutamic acid (Pyr), carbobenzoxyl (Z), succinic acid, and sulfurylation.

N-Methyl Amino Acids

N-methyl α-amino acids are important building elements of many naturally occurring antibiotics. N-methyl amino acids are known to increase pharmacokinetically useful parameters such as membrane permeability, proteolytic stability, and conformational rigidity. Most peptides can be hydrolyzed easily by digestive enzymes, or are poorly absorbed through the intestine, resulting in poor oral availability. The substitution of N-methyl amino acids can increase peptidase stability and enhance intestinal permeability.

LifeTein's methods for the preparation of N-methyl amino acids and their N-protected derivatives include the direct alkylation of Na-Boc or Cbz protected amino acids, the reductive methylation of N-benzyl amino acids followed by hydrogenolysis, or the reduction of N-Fmoc-oxazolidinones or methylol derivatives with triethylsilane in TFA. However, amino acids with reactive side chains could be difficult to handle. Therefore, different strategies of side chain protection or assembly should be adopted for each amino acid to guarantee successful synthesis.

Peptide synthesis: N Methyl modifications

  • {Cys(Me)}, SMC
  • {ADMA},{Arg(Me)2} asymmetrical
  • {SDMA},{Arg(Me)2} symmetrical
  • {Arg(Me)}
  • {Thr(Me)}
  • {Ser(Me)}
  • {Lys(Me)}
  • {Lys(Me2)}
  • {Lys(Me3)}
  • {L-1-Me-Trp}
  • {L-2-Me-Trp}
  • {D-2-Me-Trp}
  • {Tyr(Me)}
  • {Tyr(Et)}
  • {D-Tyr(Et)}
  • {Orn(Me)3}
  • {N-Me-Gly}, Sar
  • {N-Me-Ser}
  • {N-Me-Tyr}
  • {N-Me-Thr}
  • {N-Me-Asp}
  • {N-Me-Glu}
  • {N-Me-Ala}
  • {N-Me-Phe}
  • {N-Me-Leu}
  • {N-Me-Ile}
  • {N-Me-Val}
  • {N-Me-Met}
  • {N-Me-Nle}
  • {N-Me-Nva}
  • More...

Unusual amino acids incorporated into a peptide can:

  • Improve receptor binding and selectivity due to reduced backbone flexibility
  • Increase in vivo half-life by inhibiting hydrogen bonding
  • Enhance transport across cell membranes or diffuse across the blood-brain barrier

Special amino acids

  • {Cys(Cam)}
  • {D-Cys(Cam)
  • {Cys(Acm)}
  • {Cys(tBu)}
  • {Cys(StBu)}
  • {Cys(Nitosothiols)}
  • {Cys(Pyrene-Maleimide)}
  • {Gamma-Glu}
  • {D-Gamma-Glu}
  • {Beta-Asp}
  • {D-Beta-Asp}
  • {Met(O)}
  • {D-Met(O)}
  • {Lys(Ac)}
  • {Ac-Lys}
  • {Lys(Dde)}
  • {Gly(allyl)}
  • {D-Gly(allyl)}
  • {Cpg}, Cyclopentylglycine
  • {Tle}
  • {Ser(Octanoic acid)}
  • {Ser(Lipoic acid)}
  • {D-Ser(Octanoic acid)}
  • {3-Ala(2-thienyl)-OH}
  • {3-Ala(3-thienyl)-OH}
  • {Aib}
  • {Abu}
  • {D-Abu}
  • {Hyp}
  • {Phg}
  • {D-Phg}
  • {Nva}
  • {D-Nva}
  • {Nle}
  • {D-Nle}
  • {Cit}
  • {D-Cit}
  • {Orn}
  • {D-Orn}
  • {Pen}
  • {D-Pen}
  • {Cha}
  • {D-Cha}
  • {Chg}
  • {D-Chg}
  • {Dab}
  • {Dap}
  • {Pra}
  • {D-Pra}
  • {Allo-Thr}
  • {D-Allo-Thr}
  • More...
  • Biotin (N terminus)
  • DeThioBiotin
  • EDBiotin (C terminus)
  • Lys(Biotin) (middle)
  • Lys(Biotin) (C terminus)
  • Lys(LC-Biotin) (middle)
  • Lys(LC-Biotin) (C terminus)
  • Lys(Biotin) (N terminus)
  • Biotin-LC (N terminus)
  • Orn(Bio)
  • -NH-PEG3-Bio
  • FITC (N terminus)
  • EDFITC (C terminus)
  • Lys(FITC) (middle)
  • Lys(FITC) (C terminus)
  • Lys(FITC) (N terminus)
  • FITC-LC (N terminus)
  • 5-FAM (N terminus)
  • 6-FAM (N terminus)
  • ED5-FAM (C terminus)
  • Lys(5-FAM) (middle)
  • Lys(5,6-FAM)
  • Lys(5-FAM) (C terminus)
  • Lys(5-FAM) (N terminus)
  • 5-FAM-LC (N terminus)
  • Dansyl (N terminus)
  • EDDansyl (C terminus)
  • Lys(Dansyl) (middle)
  • Lys(Dansyl) (C terminus)
  • Lys(Dansyl) (N terminus)
  • Dansyl-LC (N terminus)
  • TAMRA (N terminus)
  • 5(6)-TAMTA-
  • EDTAMRA (C terminus)
  • Lys(TAMRA) (middle)
  • Lys(TAMRA) (C terminus)
  • Lys(TAMRA) (N terminus)
  • TAMRA-LC (N terminus)
  • Lys(Dnp) (middle)
  • D-Lys(Dnp) (middle)
  • Dab(Dnp) (middle)
  • Dap(Dnp) (middle)
  • EDDnp (C terminus)
  • MCA (N terminus)
  • Lys(MCA) (middle)
  • Lys(MCA) (C terminus)
  • Lys(MCA) (N terminus)
  • 3-Indolylacetic acid (N terminus)
  • Cys(Npys) (N terminus)
  • PyBA- (N terminus), 1-pyrenebutyric acid
  • Lys(PyBA)
  • Fa- (N terminus), 3-[2-2furyl]acrylic acid
  • Rhodamine B- (N terminus)
  • Lys(Rhodamine B)
  • More...

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