Publications

2025

Intramolecular N–O Bond Formation for the Synthesis of N-Alkyl and N-Aryl Isoxazolidines

Margaret Solecki, and David Crich

J. Am. Chem. Soc. 2025

Synthesis of Methyl Aprabiosaminide and 2-Hydroxyapramycin from Apramacyn

Niteshlal Kasdekar, Michael R. Spieker, Andrea Vasella, Sven N. Hobbie, and David Crich

Org. Lett. 2025, 27, 1818-1922

The Stereoselectivity of Neighboring Group-Directed Glycosylation Is Concentration Dependent

Pallabita Basu, and David Crich

J. Am. Chem. Soc. 2025, 147, 5808-5818

Why Are 5-Thioglycopyranosyl Donors More Axially Selective than their Glycopyranosyl Counterparts? A Low and Variable Temperature NMR and Computational Study

Daniil Ahiadorme, R. Houston Givhan, Henry F. Scahefer III, and David Crich

JACS Au 2025, 5, 871-889

2024

John H. O'Brien, Renuka Kadirvelaj, Po-Sen Tseng, Nolan Ross-Keppinen, David Crich, Richard M. Walsh Jr., Zachary A. Wood

Cryo-EM Structure of Recombinantly Expressed hUGDH Unveils a Hidden, Alternative Allosteric Inhibitor

Biochemistry 2025, 64, 92–104

Pratim Kumar Das, Daniil A. Ahiadorme, Niteshlal Kasdekar, Jayashree Rajput, Madhuri Vangala, David Crich and Srinivas Hotha

[Au]/[Ag]-Catalyzed Glycosidation of Ethynylcyclohexyl Glycosyl Carbonates Enables Direct Stereoselective Synthesis of 2-Azido-2-deoxy-β-mannopyranosides

Org. Lett. 2024, 26, 11034–11039

Michel Plattner, Maurizio Catelani, Sarah Lisa Gmur, Maximilian Hartmann, Fatmanur Kilic, Klara Haldimann, David Crich and Sven N. Hobbie

Phenotypic Differentiation Within the aac(6′) Aminoglycoside Resistance Gene Family Suggests a Novel Subtype IV of Contemporary Clinical Relevance

Antibiotics 2024, 13, 1196

Thomas D. Beckler and David Crich

Synthesis of N-Alkyl-1,3-dihydro-2,1-benzisoxazoles

Org. Lett. 2024, 24, 9722-9727

Daniil Ahiadorme and David Crich

Entropy-Enthalpy Compensation in the Methyl 5-Thio-α-D-galactopyranoside–Jacalin Interaction

Carb. Res. 2024, 109305

David Crich

Chemical synthesis-based structure correction of a claimed protein-free antifreeze oligosaccharide

National Science Review, 2024

Jarvis Hill, R. Houston Givhan, Bin Yi, Robert M. Jones, Eugene F. Douglass, Yaguang Xi, Henry F. Schaefer III, and David Crich

Computationally Driven Discovery of a BCR-ABL1 Kinase Inhibitor with Activity in Multidrug-Resistant Chronic Myeloid Leukemia

J. Med. Chem. 2024, 67, 19, 17820–17832

Niteshlal Kasdekar, Michael R. Spieker, and David Crich

Practical Synthesis from Streptomycin and Regioselective Partial Deprotections of (−)-(1R,2S,3R,4R,5S,6S)-1,3-Di(deamino)-1,3-diazido-2,5,6-tri-O-benzylstreptamine

J. Org. Chem. 2024, 89, 6, 4225–4231

Sonja Gross, Sebastian Herren, Marina Gysin, Anna Rominski, Anna Roditscheff, Martin Risch, Frank Imkamp, David Crich and Sven N. Hobbie

In vitro susceptibility of Neisseria gonorrhoeae to netilmicin and etimicin in comparison to gentamicin and other aminoglycosides

Microbiol Infect Dis, 2024, 43, 821–828

Omar Awad Alsaidan, Emmanuel Onobun, Chenming Ye, Lei Lou, Zanna Beharry, Zhong-Ru Xie, Iryna Lebedyeva, David Crich, Houjian Cai

Inhibition of N‐myristoyltransferase activity promotes
androgen receptor degradation in prostate cance

The Prostate. 2024, 84, 254-268

Ruslans Muhamadejevs, Klara Haldimann, Marina Gysin, David Crich, Kristaps Jaudzems, and Sven N. Hobbie

Experimental Determination of the pKa Values of Clinically Relevant Aminoglycoside Antibiotics: Toward Establishing pKa─Activity Relationships

ACS Omega 2024, 9, 5, 5876–5887

2023

Atypical N-Alkyl to N-Noralkoxy Switch in a Dual cSRC/BCR-ABL1 Kinase Inhibitor Improves Drug Efflux and hERG Affinity

Jarvis Hill, Robert M. Jones, and David Crich

ACS Med. Chem. Lett. 2023, 14, 12, 1869–1875

Discovery of a Hydroxylamine-Based Brain-Penetrant EGFR Inhibitor for Metastatic Non-Small-Cell Lung Cancer

Jarvis Hill, Robert M. Jones, and David Crich

J. Med. Chem. 2023, 66, 22, 15477–15492

Synthesis and Evaluation of Novel 5-O-(4-C-Aminoalkyl-β-D-ribofuranosyl) Apramycin Derivatives for the Inhibition of Gram-Negative Pathogens Carrying the Aminoglycoside Phosphotransferase(3′)-Ia Resistance Determinant

Dmitrijs Lubriks, Klara Haldimann, Fatmanur Kiliç, Maximilian Hartmann, Erik C. Böttger, Sven N. Hobbie, Edgars Suna, and David Crich

Helv. Chim. Acta 2023, 106, e202300138

Stereodirecting Effect of Esters at the 4-Position of Galacto- and Glucopyranosyl Donors: Effect of 4-C-Methylation on Side-Chain Conformation and Donor Reactivity, and Influence of Concentration and Stoichiometry on Distal Group Participation

Chennaiah Ande and David Crich

J. Org. Chem. 2023, 88, 19, 13883–13893

Synthesis of Gentamicins C1, C2, and C2a and Antiribosomal and Antibacterial Activity of Gentamicins B1, C1, C1a, C2, C2a, C2b, and X2

Santanu Jana, Parasuraman Rajasekaran, Klara Haldimann, Andrea Vasella, Erik C. Böttger, Sven N. Hobbie, and David Crich

ACS Infect. Dis. 2023, 9, 8, 1622–1633

Synthesis of 4-O-(4-amino-4-deoxy-ß-D-xylopyranosyl)paromomycin and 4-S-(ß-D-xylopyranosyl)-4-deoxy-4' -thio-paromomycin and evaluation of their antiribosomal and antibacterial activity

Rukshana Mohamad-Ramshan, Chennaiah Ande, Takahiko Matsushita, Klara Haldimann, Andrea Vasella, Sven N. Hobbie, and David Crich

Tetrahedron 2023, 135, 133330

Recent Advances in the Synthesis of Di- and Trisubstituted Hydroxylamines

Jarvis Hill, Thomas D. Beckler, and David Crich

Molecules 2023, 28(6), 2816

Can Side-Chain Conformation and Glycosylation Selectivity of Hexopyranosyl Donors Be Controlled with a Dummy Ligand?

Kapil Upadhyaya, Nicolas Osorio-Morales, and David Crich

J. Org. Chem. 2023, 88, 6, 3678–3696

Synthesis and evaluation of 1,5-dithialaminaribiose and -triose tetravalent constructs

Daniil Ahiadorme, Chennaiah Ande, Rafael Fernandez-Botran, and David Crich

Carb. Res. 2023, 525,108781

Influence of Side Chain Conformation on the Activity of Glycosidase Inhibitors

Po-Sen Tseng, Chennaiah Ande, Kelley W. Moremen, and David Crich

Angew. Chem. 2023, 135, e202217809

Importance of Co-operative Hydrogen Bonding in the Apramycin-Ribosomal Decoding A-Site Interaction

Michael G. Pirrone, Chennaiah Ande, Klara Haldimann, Sven N. Hobbie, Andrea Vasella, Erik C. Böttger, and David Crich

ChemMedChem 2023, 18, e202200486

2022

Dmitrijs Lubriks, Klara Haldimann, Sven N. Hobbie, Andrea Vasella, Edgars Suna, and David Crich

Synthesis, Antibacterial and Antiribosomal Activity of the 3C-Aminoalkyl Modification in the Ribofuranosyl Ring of Apralogs (5-O-Ribofuranosyl Apramycins)

Antibiotics 2022, 12, 25

Santanu Jana, and David Crich

Synthesis of Gentamicin Minor Components: Gentamicin C1a and Gentamicin C2b

Org. Lett. 2022, 24, 8564–8567

Structure-Activity Relationships for 5′′ Modifications of 4,5-Aminoglycoside Antibiotics

Jonathan C. K. Quirke, Girish C. Sati, Amr Sonousi, Marina Gysin, Klara Haldimann, Erik C. Böttger, Andrea Vasella, Sven N. Hobbie, David Crich

ChemMedChem 2022, 17, e202200120

Influence of 3-Thio Substituents on Benzylidene-Directed Mannosylation. Isolation of a Bridged Pyridinium Ion and Effects of 3-O-Picolyl and 3-S-Picolyl Esters

Timothy F. McMillan, and David Crich

EurJOC 2022, 20, e202200320

The N,N,O-Trisubstituted Hydroxylamine Isostere and Its Influence on Lipophilicity and Related Parameters

Jarvis Hill, and David Crich

ACS Med. Chem. Lett. 2022, 13, 799–806

Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-epi-Acetaminic Acid, and 8-epi-Legionaminic Acid Glycosyl Donors from N-Acetylneuraminic Acid by Side Chain Exchange

Sameera Siyabalapitiya Arachchige, and David Crich

Org. Lett. 2022, 24, 2998–3002

Intramolecular Displacement Reactions Involving Sulfur Leading to the Formation of 3,6-Thiaanhydro Sugar Derivatives during the Synthesis of 3,5-Dithio-glucofuranose

Xiaoxiao Liao, Kai Yuan, and David Crich

EurJOC 2022, e202101496

Synthesis of 10-Aza-9-oxakalkitoxin by N–O Bond Formation

Kapil Upadhyaya, and David Crich

Org. Lett. 2022, 24, 1899–1836

Exploring Noncovalent Protease Inhibitors for the Treatment of Severe Acute Respiratory Syndrome and Severe Acute Respiratory Syndrome-Like Coronaviruses

Brendan T. Freitas, Daniil A. Ahiadorme, Rahul S. Bagul, Ian A. Durie, Samir Ghosh, Jarvis Hill, Naomi E. Kramer, Jackelyn Murray, Brady M. O’Boyle, Emmanuel Onobun, Michael G. Pirrone, Justin D. Shepard, Suzanne Enos, Yagya P. Subedi, Kapil Upadhyaya, Ralph A. Tripp, Brian S. Cummings, David Crich, Scott D. Pegan

ACS Infect. Dis. 2022, 8, 596–611

Unusual C–C bond cleavage of an α-trifloxy Sialic acid hemiacetal under Lattrell-Dax conditions

Santanu Jana, David Crich

Carb. Res. 2022, 511, 108494

Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides

Sameera Siyabalapitiya Arachchige, and David Crich

J. Org. Chem 2022, 87, 316–339

2021

Polyphenols as potential inhibitors of SARS-CoV-2 RNA dependent RNA polymerase (RdRp)

Yifei Wu, David Crich, Scott D Pegan, Lei Lou, Madelyn C Hansen, Carson Booth, Ellison Desrochers, Lauren Nicole Mullininx, Edward B Starling, Kuan Y Chang, Zhong-Ru Xie

Molecules 2021, 26, 7438

Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion by 1H and 13C NMR Spectroscopy: Importance of Conformation on Participation by Distal Esters

Kapil Upadhyaya, Yagya P Subedi, David Crich

Angew. Chem. Int. Ed. 2021, 60, 25397–25403

Antibacterial activity of apramycin at acidic pH warrants wide therapeutic window in the treatment of complicated urinary tract infections and acute pyelonephritis

Katja Becker, Sha Cao, Anna Nilsson, Maria Erlandsson, Sven-Kevin Hotop, Janis Kuka, Jon Hansen, Klara Haldimann, Solveiga Grinberga, Talia Berruga-Fernández, Douglas L Huseby, Reza Shariatgorji, Evelina Lindmark, Björn Platzack, Erik C Böttger, David Crich, Lena E Friberg, Carina Vingsbo Lundberg, Diarmaid Hughes, Mark Brönstrup, Per E Andrén, Edgars Liepinsh, Sven N Hobbie

EBioMedicine 2021, 73, 103652

Guidelines for O-Glycoside Formation from First Principles

Peter R Andreana, David Crich

ACS Cent. Sci. 2021, 7, 1454-1462

GH47 and other glycoside hydrolases catalyze glycosidic bond cleavage with the assistance of substrate super-arming at the transition state

Jonathan CK Quirke, David Crich

ACS catal. 2021, 11, 10308–10315

Influence of Configuration at the 4- and 6-Positions on the Conformation and Anomeric Reactivity and Selectivity of 7-Deoxyheptopyranosyl Donors: Discovery of a Highly Equatorially Selective L-glycero-D-gluco-Heptopyranosyl Donor

Kapil Upadhyaya, Rahul S Bagul, David Crich

J. Org. Chem. 2021, 86, 12199–12225

Synthesis of O-tert-Butyl-N,N-disubstituted Hydroxylamines by N–O Bond Formation

Jarvis Hill, David Crich

Org. Lett. 2021, 23, 6396–6400

Synthesis and Antibacterial Activity of Propylamycin Derivatives Functionalized at the 5′′- and Other Positions with a View to Overcoming Resistance Due to Aminoglycoside Modifying Enzymes

Dimitrijs Lubriks, Rimants Zogota, Vikram A Sarpe, Takahiko Matsushita, Girish C Sati, Klara Haldimann, Marina Gysin, Erik C Böttger, Andrea Vasella, Edgars Suna, Sven N Hobbie, David Crich

ACS Infect. Dis. 2021, 7, 2413–2424

Side chain conformation restriction in the catalysis of glycosidic bond formation by Leloir glycosyltransferases, glycoside phosphorylases, and transglycosidases

Jonathan CK Quirke, David Crich

ACS Catal. 2021, 11, 5069–5078

Influence of substitution at the 5α-Position on the side chain conformation of glucopyranosides

Parasuraman Rajasekaran, Michael G Pirrone, David Crich

Carb. Res. 2021, 500, 108254

An Advanced Apralog with Increased in vitro and in vivo Activity toward Gram‐negative Pathogens and Reduced ex vivo Cochleotoxicity

Amr Sonousi, Jonathan CK Quirke, Prabuddha Waduge, Tanja Janusic, Marina Gysin, Klara Haldimann, Shan Xu, Sven N Hobbie, Su‐Hua Sha, Jochen Schacht, Christine S Chow, Andrea Vasella, Erik C Böttger, David Crich

ChemMedChem 2021, 16, 335-339

Polyphenols as alternative treatments of COVID-19

Yifei Wu, Scott D Pegan, David Crich, Ellison Desrochers, Edward B Starling, Madelyn C Hansen, Carson Booth, Lauren Nicole Mullininx, Lei Lou, Kuan Y Chang, Zhong-Ru Xie

Comput. Struct. Biotechnol. J. 2021, 19, 5371-5380