Method for peptide synthesis and apparatus for carrying out a method for solid phase synthesis of peptides
AssigneeSulfotools GmbH
InventorsSascha Knauer, Tobias Michael Louis Roese, Olga Avrutina, Harald Kolmar, Christina Uth
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Abstract
The invention relates to a method for peptide synthesis, wherein said method comprises the steps of reacting a first amino acid or a first peptide with an α-amine protected second amino acid in a solvent selected from the group consisting of water, alcohol, and a mixture of water and alcohol, and removing the α-amine protecting group with a deprotecting solution. The invention further relates to protective agents, their use and an apparatus for carrying out a method for solid phase synthesis of peptides.
Claims13
A method of forming protecting groups on functional groups during water-based peptide synthesis, the method comprising using a protective agent,
- wherein the protective agent comprises
- a) a backbone structure,
- b) at least two water-solubility enhancing functional groups and
- c) at least one reactive group,
- wherein the backbone structure comprises a moiety selected from the group consisting of 9-methylfluorene, and/or di- or triphenylmethane,
- wherein the at least two water-solubility enhancing functional groups are selected from SO3−, PO32−, N(CH3)2, N(CH3)3+, CN, OSO3− ester, OPO32− ester and combinations thereof, and
- wherein the water-solubility enhancing functional group and the reactive group are attached to the backbone structure via at least one covalent bond,
- for protecting a functional group in a water-based reaction of a first amino acid or first peptide with an α-amine protected second amino acid or α-amine protected second peptide,
- wherein the protective agent forms protecting groups on at least one of said α-amino functional group during the water-based reaction of said first amino acid or first peptide with said α-amine protected second amino acid or α-amine protected second peptide, and
- wherein the C-terminus of said first amino acid or first peptide is anchored to an insoluble support.
Protective agent suitable for forming protecting groups on functional groups on a peptide and/or amino acid during water based peptide synthesis,
- wherein the protective agent comprises
- a) a backbone structure,
- b) at least two water-solubility enhancing functional group and
- c) at least one reactive group,
- wherein the backbone structure comprises a moiety selected from the group consisting of 9-methylfluorene, t-butane and/or mono-, di or triphenylmethane,
- wherein the water-solubility enhancing functional group is selected from the group consisting of SO3−, PO32−, N(CH3)2, N(CH3)3+, CN, OSO3− ester, OPO32− ester and combinations thereof, and
- wherein the water-solubility enhancing functional group and the reactive group are attached to the backbone structure via at least one covalent bond.
A method of forming protecting groups on functional groups during water-based peptide synthesis, the method comprising using a protective agent,
- wherein the protective agent comprises
- a) a backbone structure,
- b) at least two water-solubility enhancing functional groups and
- c) at least one reactive group,
- wherein the backbone structure comprises a moiety selected from the group consisting of 9-methylfluorene, and/or di- or triphenylmethane,
- wherein the water-solubility enhancing functional groups are selected from SO3−, PO32−, N(CH3)2, N(CH3)3+, CN, OSO3− ester, OPO32− ester and combinations thereof, and
- wherein the water-solubility enhancing functional group and the reactive group are attached to the backbone structure via at least one covalent bond,
- for protecting a functional group in a water-based reaction of a first amino acid or first peptide with an α-amine protected second amino acid or α-amine protected second peptide,
- wherein said water based peptide synthesis is a peptide synthesis in a solvent limited to a solvent selected from the group consisting of water, alcohol and mixtures of water and alcohol;
- and wherein the protective agent enhances solubility of said second peptide or said second amino acid in said solvent, wherein using said protective agent for protecting a functional group in said water-based reaction comprises protecting said at least one of said α-amino functional group of said second peptide or said second amino acid with said protective agent prior to coupling said second peptide or said second amino acid with said first peptide or said first amino acid in said solvent.
Dependencies are inferred from the claim text.