Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides

A method of producing a polypeptide comprising at least one amino acid having a structure of Formula (I):

• the method comprising incorporating the amino acid of Formula (I) into a terminal or internal position within the polypeptide, wherein:
• A is
• arylene,
• substituted arylene;
• B is a linker selected from the group consisting of lower alkylene, substituted lower alkylene, lower alkenylene, substituted lower alkenylene, lower heteroalkylene, substituted lower heteroalkylene, —S—, —S-(alkylene or substituted alkylene)-, —S(O)k— where k is 1, 2, or 3, —S(O)k(alkylene or substituted alkylene)- where k is 1, 2, or 3, —C(O)—, —C(O)-(alkylene or substituted alkylene), —N(R′)—, —NR′-(alkylene or substituted alkylene)-, —C(O)N(R′)—, —CON(R′)-(alkylene or substituted alkylene)-, —C(R′)═N—, and —C(R′)═N—N(R′), where each R′ is independently H, alkyl, or substituted alkyl;
• J is
• R is H, alkyl, substituted alkyl, cycloalkyl, or substituted cycloalkyl;
• each R″ is independently H, alkyl, substituted alkyl, or a protecting group, or when more than one R″ group is present, two R″ optionally form a heterocycloalkyl;
• R1 is H, an amino protecting group, or at least one amino acid;
• and
• R2 is OH, an ester protecting group, or at least one amino acid;
• each of R3 and R4 is independently H, halogen, lower alkyl, or substituted lower alkyl, or R3 and R4 or two R3 groups optionally form a cycloalkyl or a heterocycloalkyl;
• or the -A-B-J-R groups together form a bicyclic or tricyclic cycloalkyl or heterocycloalkyl comprising at least one carbonyl group, including a dicarbonyl group, protected carbonyl group, including a protected dicarbonyl group, or masked carbonyl group, including a masked dicarbonyl group;
• or the -J-R group together forms a monocyclic or bicyclic cycloalkyl or heterocycloalkyl comprising at least one carbonyl group, including a dicarbonyl group, protected carbonyl group, including a protected dicarbonyl group, or masked carbonyl group, including a masked dicarbonyl group.