Efficient Covalent Bond Formation in Gas-Phase Peptide-Peptide Ion Complexes with the Photoleucine Stapler

Journal of the American Society for Mass Spectrometry
Christopher J ShafferFrantisek Turecek

Abstract

Noncovalent complexes of hydrophobic peptides GLLLG and GLLLK with photoleucine (L*) tagged peptides G(L* n L m )K (n = 1,3, m = 2,0) were generated as singly charged ions in the gas phase and probed by photodissociation at 355 nm. Carbene intermediates produced by photodissociative loss of N2 from the L* diazirine rings underwent insertion into X-H bonds of the target peptide moiety, forming covalent adducts with yields reaching 30%. Gas-phase sequencing of the covalent adducts revealed preferred bond formation at the C-terminal residue of the target peptide. Site-selective carbene insertion was achieved by placing the L* residue in different positions along the photopeptide chain, and the residues in the target peptide undergoing carbene insertion were identified by gas-phase ion sequencing that was aided by specific (13)C labeling. Density functional theory calculations indicated that noncovalent binding to GL*L*L*K resulted in substantial changes of the (GLLLK + H)(+) ground state conformation. The peptide moieties in [GL*L*LK + GLLLK + H](+) ion complexes were held together by hydrogen bonds, whereas dispersion interactions of the nonpolar groups were only secondary in ground-state 0 K structures. Born-Oppenheimer molecula...Continue Reading

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Citations

Jun 21, 2017·Journal of Mass Spectrometry : JMS·Robert PepinFrantišek Tureček
Nov 12, 2017·Journal of the American Society for Mass Spectrometry·Alexander D JacobsDavid E Clemmer
Apr 5, 2019·Journal of the American Society for Mass Spectrometry·Yang Liu, František Tureček
Oct 15, 2019·International Journal of Mass Spectrometry·Lance E TalbertRyan R Julian
May 8, 2018·Journal of the American Society for Mass Spectrometry·Huong T H NguyenFrantišek Tureček

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