Abstract
The synthetic cyclic octapeptide octreotide is less stable under UV and fluorescent lights than its naturally occurring derivative somatostatin. Upon irradiation at λ > 290 nm, and in the presence of oxygen, octreotide is quickly transformed into a photoproduct showing an increase of mass of 16 Da. The increase of 16 Da to the mass of octreotide is related to a complex transformation where (i) the side chain of d-Trp is transferred onto the side chain of the Lys residue and (ii) the former d-Trp residue is transformed into hydroxyglycine, which ultimately fragments. The complex sequence of phototransformation is orchestrated by the presence of d-Trp and the unusual orientation of its carbonyl group toward the disulfide bond. The phototransformation of octreotide is illustrated by product A.
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