Solid phase synthesis of two muramyl pentapeptide derivatives

Szulc, Monika; Samaszko-Fiertek, Justyna; Ślusarz, Rafał; Kowalska, Kornelia; Sikorski, Artur; Madaj, Janusz

doi:10.1080/07328303.2016.1154153

Cited by 1 publication

(2 citation statements)

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“…Further work that tried to explain this mechanism used increasingly complex research models with an increasingly longer peptidoglycan chain, such as the Whitesides study [16], in which they used a tripeptide including lysine. In our study on this mechanism, we decided to use the muramyl pentapeptide derivative, the synthesis, and characteristics of which we described in our earlier work [17]. On the other hand, studies of the activity of vancomycin analogues modified in the sugar part show increased effectiveness, as pointed out by Min Ge and co-authors [11].…”

Section: Resultsmentioning

confidence: 99%

“…For the MD simulations we have parameterized all non-standard groups and fragments for the AMBER [38] ff03.r1 [39,40] and glycam06g [41,42] force fields as described in detail in [25]. In the crystallographic complex of vancomycin with di-acetyl-Lys-D-Ala-D-Ala ligand (PDB ID 1FVM, chain O) the ligand structure has been replaced with muramyl pentapeptide derivative described in [17,25] of the sequence: Mur-Ala-D-iGlu-Lys-D-Ala-D-Ala. Vancomycin vancosamine and the Lys side chain amine groups were protonated.…”

Section: Simulationsmentioning

confidence: 99%

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NMR and MD Analysis of the Bonding Interaction of Vancomycin with Muramyl Pentapeptide

Ślusarz

Dmochowska

Samaszko-Fiertek

et al. 2022

IJMS

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The article describes an NMR spectroscopy study of interactions between vancomycin and a muramyl pentapeptide in two complexes: vancomycin and a native muramyl pentapeptide ended with D-alanine (MPP-D-Ala), and vancomycin and a modified muramyl pentapeptide ended with D-serine (MPP-D-Ser). The measurements were made in a 9:1 mixture of H2O and D2O. The obtained results confirmed the presence of hydrogen bonds previously described in the literature. At the same time, thanks to the pentapeptide model used, we were able to prove the presence of two more hydrogen bonds formed by the side chain amino group of L-lysine and oxygen atoms from the vancomycin carboxyl and amide groups. This type of interaction has not been described before. The existence of these hydrogen bonds was confirmed by the 1H NMR and molecular modeling. The formation of these bonds incurs additional through-space interactions, visible in the NOESY spectrum, between the protons of the L-lysine amino group and a vancomycin-facing hydrogen atom in the benzylic position. The presence of such interactions was also confirmed by molecular dynamics trajectory analysis.

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Section: Resultsmentioning

confidence: 99%