Peptide compound production method
AssigneeChubu University Educational Foundation
InventorsHisashi YAMAMOTO, Tomohiro HATTORI
Life of this patent
Estimating the term…
Abstract
Provided is a method that prevents decreases in solubility in an organic solvent when elongating a peptide chain by a peptide coupling reaction and improves the reactivity of a peptide chain and the operability in a purification process. The method makes it possible to obtain a polypeptide compound represented by formula (P1) by performing amide formation reaction of the carboxyl group on the right side of the amino acid or the peptide compound in formula (R1) with the amino group on the left side of the amino acid or the peptide ester compound in formula (R2) in which the terminal carboxyl group is protected by a silicon-containing hydrophobic substituent TAG(Si).
Claims22
A method for producing a polypeptide compound, comprising the step of causing an amide forming reaction between the carboxyl group on the right side of an amino acid or peptide compound represented by formula (R1) and the amino group on the left side of represented by formula (R2) amino acid ester or peptide ester compound to produce a peptide compound represented by formula (P1),
- wherein, in formula (R1),
- Ta represents a hydrogen atom or monovalent substituent,
- R11 and R12 each represent, independently of each other, a hydrogen atom, halogen atom, hydroxyl group, carboxyl group, nitro group, cyano group, or thiol group, or an amino group, monovalent aliphatic hydrocarbon group, monovalent aromatic hydrocarbon group, or monovalent heterocyclic group that may have one or more substituents,
- R13 represents a hydrogen atom, carboxyl group, hydroxyl group, or a monovalent aliphatic hydrocarbon group, aromatic hydrocarbon group, or heterocyclic group that may have one or more substituents and may be bound to the nitrogen atom via a linking group,
- or
- R11 and R13 may be bound to each other to form, together with the carbon atom to which R11 binds and the nitrogen atom to which R13 binds, a heterocyclic group that may have one or more substituents,
- A11 and A12 each represent, independently of each other, a divalent aliphatic hydrocarbon group that may have one or more substituents having 1 to 3 carbon atoms,
- p11 and p12 each represent, independently of each other, 0 or 1, and
- n1 represents an integer of equal to or greater than 1 corresponding to the number of the structure units parenthesized with [ ], provided that when n1 is equal to or greater than 2, then the two or more structure units in [ ] may be either identical to each other or different from each other,
- wherein, in formula (R2),
- Tb represents a hydrogen atom or monovalent substituent,
- R21 and R22 each represent, independently of each other, a hydrogen atom, halogen atom, hydroxyl group, carboxyl group, nitro group, cyano group, or thiol group, or an amino group, monovalent aliphatic hydrocarbon group, monovalent aromatic hydrocarbon group, or monovalent heterocyclic group that may have one or more substituents,
- R23 represents a hydrogen atom, carboxyl group, hydroxyl group, or a monovalent aliphatic hydrocarbon group, aromatic hydrocarbon group, or heterocyclic group that may have one or more substituents and may be bound to the nitrogen atom via a linking group,
- or
- R21 and R23 may be bound to each other to form, together with the carbon atom to which R21 binds and the nitrogen atom to which R23 binds, a heterocyclic group that may have one or more substituents,
- A21 and A22 each represent, independently of each other, a divalent aliphatic hydrocarbon group that may have one or more substituents having 1 to 3 carbon atoms,
- p21 and p22 each represent, independently of each other, 0 or 1, and
- n2 represents an integer of equal to or greater than 1 corresponding to the number of the structure units parenthesized with [ ], provided that when n2 is equal to or greater than 2, then the two or more structure units in [ ] may be either identical to each other or different from each other, provided that
- (i) Ta is a group represented by —O—C(═O)-TAG(Si) and/or
- (ii) Tb is a group represented by -TAG(Si),
- where -TAG(Si) has the following structure,
- wherein, in formula (T),
- Rx represents a divalent, trivalent, or tetravalent aliphatic hydrocarbon group, aromatic hydrocarbon group, or heterocyclic group that may have one or more substituents,
- L represents a single bond or a divalent linking group,
- mx represents an integer of 0 or 1 provided that when mx is 0, L is a single bond,
- Z represent, independently of each other, a carbon atom (C) or a silicon atom (Si),
- Rz1, Rz2, and Rz3 represent, independently of each other, a monovalent aliphatic hydrocarbon group, aromatic hydrocarbon group, silicon-containing hydrocarbon group, or heterocyclic group that may have one or more substituents,
- provided that the three parenthesized substituents in —Z(Rz1)(Rz2)(Rz3) may either be the same as each other or different from each other,
- nx represents an integer of 1 to 3 corresponding to the number of the substituents parenthesized with { }, provided that when mx is 2 or 3, then the two or three substituents parenthesized with { } in formula (T) may either be the same as each other or different from each other,
- wherein, in formula (P1),
- Ta, R11, R12, R13, A11, A12, p11, p12, and n1 each represent the same definitions as those of the same symbols in general formula (R1) above, and
- R21, R22, R23, A21, A22, p21, p22, n2, and Tb each represent the same definitions as those of the same symbols in general formula (R2) above.
13-14. (canceled)
16-17. (canceled)
Dependencies are inferred from the claim text.