Amino acid having functional group capable of intermolecular hydrogen bonding, peptide compound containing same and method for production thereof

An amino acid represented by Formula A below:

• wherein
• R1 is hydrogen, C1-C6 alkyl, or a group represented by Formula 1 or Formula 2, and, in this case, as for R2A and R2B, R2A is hydrogen, C1-C6 alkyl, or a group represented by Formula 1 or Formula 2, and R2B is hydrogen or C1-C6 alkyl, or R2A and R2B form a 4- to 6-membered ring together with the carbon atom to which they are bonded, or
• R1 forms a 4- to 6-membered hetero ring together with the nitrogen atom to which R1 is bonded, R2A and the carbon atom to which R2A is bonded, and the hetero ring optionally has one or more substituents selected from the group consisting of a group represented by Formula 1 or Formula 2, —OH, and an alkoxy group, and, in this case, R2B is hydrogen or C1-C6 alkyl;
• R3 is a single bond or —CHR4—;
• R4 is hydrogen, C1-C4 alkyl, or a group represented by Formula 1 or Formula 2;
• Formula 1 and Formula 2 are respectively represented by the following formulae:
• wherein
• * indicates a point of bonding;
• Q1 and Q2 are independently a single bond, C1-C4 alkylene, or C2-C4 heteroalkylene containing one oxygen atom;
• A1 is —O— or —S—;
• L1 is linear C1-C3 alkylene optionally substituted with one or more substituents selected from the group consisting of fluorine, C1-C2 alkyl, C1-C2 fluoroalkyl, and oxo (═O);
• A2 is a single bond, —O—, or —S—;
• L2 is a single bond or linear C1-C3 alkylene optionally substituted with one or more substituents selected from the group consisting of fluorine, C1-C2 alkyl, C1-C2 fluoroalkyl, and oxo (═O);
• X is —OH, —NRZ1RZ2, —CONRZ1RZ2, or 5- to 6-membered saturated or unsaturated heterocyclyl containing 1 to 3 heteroatoms and optionally substituted with oxo or one or more halogens;
• RZ1 and RZ2 are independently selected from the group consisting of hydrogen, —OH, C1-C4 alkyl, and C1-C4 alkylsulfonyl;
• Y is —OH, C1-C4 alkylsulfonylamino, —NRZ3RZ4, —CONRZ3RZ4, or 5- to 6-membered saturated or unsaturated heterocyclyl containing 1 to 3 heteroatoms and optionally substituted with oxo or halogen;
• RZ3 and RZ4 are independently selected from the group consisting of hydrogen, —OH, C1-C4 alkyl, and C1-C4 alkylsulfonyl;
• and
• Z is hydrogen or C1-C4 alkyl,
• provided that when A2 is —O— or —S—, Z is not hydrogen, and
• the amino acid represented by Formula A contains at least one group represented by either Formula 1 or Formula 2.

A protected amino acid, wherein an amino group and/or a carboxyl group contained in an amino acid is protected by a protecting group, wherein the amino acid is represented by Formula A below:

• wherein
• R1 is hydrogen, C1-C6 alkyl, or a group represented by Formula 1 or Formula 2, and, in this case, as for R2A and R2B, R2A is hydrogen, C1-C6 alkyl, or a group represented by Formula 1 or Formula 2, and R2B is hydrogen or C1-C6 alkyl, or R2A and R2B form a 4- to 6-membered ring together with the carbon atom to which they are bonded, or
• R1 forms a 4- to 6-membered hetero ring together with the nitrogen atom to which R1 is bonded, R2A and the carbon atom to which R2A is bonded, and the hetero ring optionally has one or more substituents selected from the group consisting of a group represented by Formula 1 or Formula 2, —OH, and an alkoxy group, and, in this case, R2B is hydrogen or C1-C6 alkyl:
• R3 is a single bond or —CHR4—;
• R4 is hydrogen, C1-C4 alkyl, or a group represented by Formula 1 or Formula 2;
• Formula 1 and Formula 2 are respectively represented by the following formulae:
• wherein
• * indicates a point of bonding;
• Q1 and Q2 are independently a single bond, C1-C4 alkylene, or C2-C4 heteroalkylene containing one oxygen atom;
• A1 is —O— or —S—;
• L1 is linear C1-C3 alkylene optionally substituted with one or more substituents selected from the group consisting of fluorine, C1-C2 alkyl, C1-C2 fluoroalkyl, and oxo (═O);
• A2 is a single bond, —O—, or —S—;
• L2 is a single bond or linear C1-C3 alkylene optionally substituted with one or more substituents selected from the group consisting of fluorine, C1-C2 alkyl, C1-C2 fluoroalkyl, and oxo (═O);
• X is —OH, —NRZ1RZ2, —CONRZ1RZ2, or 5- to 6-membered saturated or unsaturated heterocyclyl containing 1 to 3 heteroatoms and optionally substituted with oxo or one or more halogens;
• RZ1 and RZ2 are independently selected from the group consisting of hydrogen, —OH, C1-C4 alkyl, and C1-C4 alkylsulfonyl;
• Y is —OH, C1-C4 alkylsulfonylamino, —NRZ3RZ4, —CONRZ3RZ4, or 5- to 6-membered saturated or unsaturated heterocyclyl containing 1 to 3 heteroatoms and optionally substituted with oxo or halogen;
• RZ3 and RZ4 are independently selected from the group consisting of hydrogen, —OH, C1-C4 alkyl, and C1-C4 alkylsulfonyl;
• and
• Z is hydrogen or C1-C4 alkyl,
• provided that when A2 is —O— or —S—, Z is not hydrogen, and
• the amino acid represented by Formula A contains at least one group represented by either Formula 1 or Formula 2.