Serine Octamer Substitution Reactions With α-Hydroxy Acids.

Keerthana Unni, Brison A Shira, Dylan T Holden, Thalappil Pradeep, R Graham Cooks

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Article in Rapid communications in mass spectrometry : RCM, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors.

Keerthana UnniDepartment of Chemistry, Purdue University, West Lafayette, Indiana, USA.

Brison A ShiraDepartment of Chemistry, Purdue University, West Lafayette, Indiana, USA.ORCID https://orcid.org/0000-0002-5250-5882

Dylan T HoldenDepartment of Chemistry, Purdue University, West Lafayette, Indiana, USA.

Thalappil PradeepDST Unit of Nanoscience (DST UNS) and Thematic Unit of Excellence (TUE), Department of Chemistry, Indian Institute of Technology Madras, Chennai, India.ORCID https://orcid.org/0000-0003-3174-534X

R Graham CooksDepartment of Chemistry, Purdue University, West Lafayette, Indiana, USA.ORCID https://orcid.org/0000-0002-9581-9603

Funding

Anusandhan National Research Foundation (ANRF)the Centre of Excellence on Molecular Materialsthe Multi-University Research Initiative of the Air Force Office of Scientific Research FA9550-21-1-0170the Multi-University Research Initiative of the Air Force Office of Scientific Research subaward 62741613-204669

6 · The paper itself

Abstract

rationaleThe amino acid serine forms chiral magic number clusters, which can be studied using mass spectrometry (MS). Serine octamer clusters are also known to incorporate one or two nonserine monomers with serine monomers to make up the octamer.

methodsA Thermo LTQ ion trap mass spectrometer with nanoelectrospray ionization (nESI) was used to study cluster formation by both kinetically and energy-resolved methods. This study validates past observations on the homochiral preference of serine octamer during its association with other nonserine monomers.

resultsA substrate scope covering α-hydroxy acids and related molecules was studied. The chiral preference was investigated with tandem MS and the importance of salt bridge formation and α/β-carbon hydrogen bonding was recognized.

conclusionsWeak interactions involving steric forces, salt bridges, ion-dipole interactions, and hydrogen bonds control stereoselective and chiroselective properties of the serine octamer cluster.

Identifiers

PMID42389822

DOI10.1002/rcm.70133

PMCPMC13324970

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