Article
Chemistry, Multidisciplinary
Samira Escopy, Yashapal Singh, Keith J. Stine, Alexei V. Demchenko
Summary: This research describes a direct conversion of thioglycosides using a regenerative approach, bypassing the need for bromide intermediates and heavy-metal-based promoters. The reaction conditions are mild, with only 1 equiv. NIS and catalytic HOFox needed under neutral conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Correction
Chemistry, Multidisciplinary
Gao-Lan Zhang, Madhusudhan Reddy Gadi, Xikai Cui, Ding Liu, Jiabin Zhang, Varma Saikam, Christopher Gibbons, Peng G. Wang, Lei Li
Summary: The study presents a protection-group-free method for S-glycosylation, which can be applied in the synthesis of thioglycosides and thioglycopeptides in water.
Article
Chemistry, Multidisciplinary
Peng Wen, Peijing Jia, Qiuhua Fan, Bethany J. McCarty, Weiping Tang
Summary: A streamlined iterative assembly of thio-oligosaccharides was developed by aqueous glycosylation, efficiently synthesizing 1,2-trans S-glycosides with high chemo- and stereoselectivity at room temperature. The method was successfully applied to the synthesis of a trimannoside moiety of N-linked glycans core region.
Article
Chemistry, Organic
Jianhong Zhang, Tetsuo Koyama, Takahiko Matsushita, Ken Hatano, Koji Matsuoka
Summary: Efficient synthesis of lauryl thioglycoside of Neu5Gc was achieved from a known thioglycoside of Neu5Ac. The reactivity of Neu5Gc thioglycoside in O-glycosidation was investigated, showing good activities with simple alcohols. The thioglycoside also demonstrated potential as a glycosyl donor in reactions with glucose and lactose derivatives.
TETRAHEDRON LETTERS
(2021)
Review
Chemistry, Inorganic & Nuclear
Praveen Kumar Singh, Poulomi Majumdar, Surya Prakash Singh
Summary: PPGs are beneficial tools for controlled release of bioagents, and visible/NIR light activated BODIPY PPGs with tunable spectral properties and low phototoxicity are effective for releasing protecting groups.
COORDINATION CHEMISTRY REVIEWS
(2021)
Review
Chemistry, Organic
Mehmet Murat Kisla, Mohammed Al-Kassim Hassan, Hind M. Osman, Amine Sena Aydin, Hasan Tahsin Sen, Shan Khazei, Pinar Kul, Canan Kus
Summary: The use of protecting groups in organic chemistry has been successful in synthesizing a variety of useful organic compounds and addressing complexities in organic reactions. These protecting groups find applications in simple and complex reactions involving the synthesis of large organic compounds such as peptides and oligosaccharides. Ideal protecting groups are utilized to prevent undesired reactions and achieve desired objectives.
CURRENT ORGANIC SYNTHESIS
(2023)
Review
Chemistry, Multidisciplinary
Richard J. Spears, Cliona McMahon, Vijay Chudasama
Summary: The use of protecting groups for the cysteine thiol group has allowed for advancements in peptide and protein chemistry, enabling the synthesis of complex disulfide-rich peptides, protein semisynthesis, and labeling both in vitro and in vivo. Researchers have developed over 60 individual protecting groups for cysteine, showcasing their importance in peptide synthesis and protein science.
CHEMICAL SOCIETY REVIEWS
(2021)
Review
Pharmacology & Pharmacy
J. Kenneth Hoober, Laura L. Eggink
Summary: The entry of peptides into glycobiology has led to the development of a unique class of therapeutic tools. Peptides that mimic sugars as ligands of lectin-type receptors have opened a unique approach to modulate activity of immune cells. Advantages of peptides over sugars as drugs for immune modulation will be illustrated in this review.
Article
Chemistry, Physical
Laura J. McKay, Carl-Johan Carling, Neil R. Branda
Summary: Two novel photoremovable protecting groups in the benzoin class with improved molar extinction coefficients and extended absorptions towards the visible region have been prepared, yet their characteristics may not always translate to photoresponsive efficacy.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2021)
Article
Chemistry, Physical
Zi-Gang Lu, Wenbin Chen, David Lee Phillips, Ming-De Li
Summary: In this study, blebbistatin derivatives with various electronic characteristic leaving groups were synthesized and studied to unveil the photocleavage mechanism(s) and the tunable effect of the leaving groups. The results provide a structure-property relationship that allows for rational selection of protected groups in molecules for specific applications.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Engineering, Chemical
Adrien Lusterio, Miguel Melendez-Zamudio, Michael A. Brook
Summary: The article discusses a method for converting vinylsilicones to aminoalkylsilicones using thiol-ene reactions, without the need for expensive transition metal catalysts, and the resulting products may contain residual vinyl groups.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Ivan Gallego, Javier Ramos-Soriano, Alejandro Mendez-Ardoy, Justo Cabrera-Gonzalez, Irene Lostale-Seijo, Beatriz M. Illescas, Jose J. Reina, Nazario Martin, Javier Montenegro
Summary: Fully substituted peptide/[60]fullerene hexakis-adducts have the potential for multivalent protein recognition and offer synthetically simpler alternatives to natural ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Sakonwan Kuhaudomlarp, Eike Siebs, Elena Shanina, Jeremie Topin, Ines Joachim, Priscila da Silva Figueiredo Celestino Gomes, Annabelle Varrot, Didier Rognan, Christoph Rademacher, Anne Imberty, Alexander Titz
Summary: Due to the antimicrobial resistance crisis, lectins are considered novel drug targets, with the study focusing on non-carbohydrate inhibitors for LecA. A catechol was identified as an experimentally confirmed hit, acting as a millimolar LecA inhibitor. The first co-crystal structure of a non-carbohydrate inhibitor in complex with a bacterial lectin demonstrated how the catechol mimics the binding of natural glycosides with LecA, indicating a fundamentally new class of glycomimetics.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jinhuan Dong, Mengying Jia, Xianxiu Xu
Summary: A novel strategy for the regiospecific cleavage of inert aryl C == N bonds in N-aryl amides using hypervalent iodine(V) reagents has been developed in this study, allowing for the efficient production of primary amides under mild conditions.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Sabrina Leichnitz, Komadhie C. Dissanayake, Arthur H. Winter, Peter H. Seeberger
Summary: Protective groups that can be selectively removed under mild conditions are important in carbohydrate chemistry. This study explores different BODIPY protecting groups for their usefulness in glycan synthesis. A BODIPY group with a boron difluoride unit is stable during glycosylations but can be cleaved with green light, as demonstrated by the assembly of a trisaccharide.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Amani Alhifthi, Spencer J. Williams
Summary: The study reports the pH-rate constant profile for the hydrolysis of 4-nitrophenyl beta-D-glucoside, showing different hydrolysis mechanisms and factors at different pH values.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Laura Burchill, Spencer J. Williams
Summary: Microorganisms produce a variety of lipidic species that play a crucial role in immune activity, but their structures are often incompletely defined and their supply is limited. Total synthesis can address these issues, providing high-purity samples for immunological studies.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemical Research Methods
Cheryl Frankfater, Hideji Fujiwara, Spencer J. Williams, Adriaan Minnaard, Fong-Fu Hsu
Summary: This study used high-resolution mass spectrometry to investigate the mechanisms of complex mycolic acid synthesis in Mycobacterium tuberculosis cells. By characterizing the Mtb mycolic acid family, the study identified the composition and location of functional groups in different lipid species. The findings demonstrate the capability of LIT MSn in determining the structures of complex lipids in a mixture.
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2022)
Article
Microbiology
Arashdeep Kaur, Phillip L. van der Peet, Janice W-Y Mui, Marion Herisse, Sacha Pidot, Spencer J. Williams
Summary: Sulfoglycolysis pathways allow for the breakdown and recycling of sulfoquinovose in both carbon and sulfur content. Through enrichment cultures, two gram-positive Arthrobacter spp. were discovered to produce sulfolactate as the end-product of their metabolism. Genome sequences revealed a modified sulfoglycolytic EMP gene cluster in these bacteria, expanding our understanding of the sulfo-EMP pathway to include soil bacteria.
ARCHIVES OF MICROBIOLOGY
(2022)
Article
Chemistry, Organic
Laura Burchill, Luca Zudich, Phillip L. van der Peet, Jonathan M. White, Spencer J. Williams
Summary: In this study, simple methods for synthesizing chiral hydroxy- and aminohydroxysulfonic acids were reported. The absolute configurations of naturally occurring 3-amino-2-hydroxypropanesulfonate were determined by comparing optical rotation. This research provides support for future studies on the occurrence, chemotaxonomic distribution, and metabolism of these alkylsulfonates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biotechnology & Applied Microbiology
Janice W. -Y. Mui, David P. De Souza, Eleanor C. Saunders, Malcolm J. McConville, Spencer J. Williams
Summary: The microbial degradation of sulfoquinovose through sulfoglycolysis allows the utilization of its carbon content and contributes to the biomineralization of its sulfur.
APPLIED AND ENVIRONMENTAL MICROBIOLOGY
(2023)
Article
Microbiology
Arashdeep Kaur, Nichollas E. Scott, Marion Herisse, Ethan D. Goddard-Borger, Sacha Pidot, Spencer J. Williams
Summary: This study discovered two Paenarthrobacter spp. (Paenarthrobacter nitrojuajacolis LG01 and Paenarthrobacter histidinolovorans LG02) that can degrade levoglucosan as the sole carbon source. By genome sequencing and proteomics analysis, the researchers found the expression of a series of genes encoding known levoglucosan degrading enzymes, which are generally conserved in various bacteria. The findings reveal the diversity of how bacteria utilize levoglucosan as a nutrient source.
ARCHIVES OF MICROBIOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Marion Herisse, Keishi Ishida, Jordan Staiger-Creed, Louise Judd, Spencer J. Williams, Benjamin P. Howden, Timothy P. Stinear, Hans-Martin Dahse, Kerstin Voigt, Christian Hertweck, Sacha J. Pidot
Summary: Nocardia are opportunistic human pathogens that cause difficult to treat infections. However, little is known about their involvement in the pathogenesis and the natural products they produce. In this study, a new cytotoxic and antifungal polyene called terpenomycin was discovered in a human pathogenic Nocardia terpenica isolate. The biosynthetic pathway and unique features of terpenomycin were revealed, and a mutant library helped identify a terpenomycin-null mutant. These findings highlight the potential of neglected actinomycetes as producers of diverse bioactive molecules.
ACS CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Garth Cameron, Tram Nguyen, Marcin Ciula, Spencer J. Williams, Dale I. Godfrey
Summary: Natural Killer T (NKT) cells are a type of T cell subset that recognize lipid antigens and have diverse functional properties. The commensal organism Bacteroides fragilis produces various forms of alpha-galactosylceramide (alpha GC), a lipid antigen target for NKT cells. The total synthesis of a major form of alpha GC from B. fragilis (Bf alpha GC) and several analogues was reported, and their recognition by mouse and human NKT cells was confirmed. NKT cells experienced with Bf alpha GC displayed regulatory function and inhibited the expansion of naive NKT cells and antigen-stimulated mucosal-associated invariant T (MAIT) cells, revealing the broad immunoregulatory activity of B. fragilis-derived NKT cell agonists.
Article
Crystallography
Phillip L. van der Peet, Rohan D. Joyce, Holger Ott, Sebastian M. Marcuccio, Jonathan M. White, Spencer J. Williams
Summary: The crystal structure of the title compound reveals strong hydrogen bonds and interactions, forming infinite chains along the c-axis direction.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2022)
Review
Chemistry, Organic
Laura Burchill, Spencer J. Williams
Summary: This article reviews the historical discovery of d-cysteinolic acid and related molecules, discusses their distribution and occurrence in marine and freshwater organisms, chemical synthesis routes, and summarizes the knowledge and speculations surrounding their biosynthesis, degradation, and bioconversions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Alexander J. D. Snow, Laura Burchill, Mahima Sharma, Gideon J. Davies, Spencer J. Williams
Summary: Sulfoquinovose (SQ) is a derivative of glucose produced by photosynthetic organisms, and its degradation plays a key role in the global sulfur and carbon biogeochemical cycles. Bacteria degrade SQ through two main pathways: one involves breaking down the 6-carbon skeleton of SQ into two fragments, while the other involves complete metabolism through desulfonylation to release sulfite and glucose. Discovery of sulfoglycolytic pathways has revealed novel enzymes and binding proteins, shedding light on how the sulfonate group is recognized and its relationship to glycolysis pathways.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Organic
Dylan G. M. Smith, Emi Ito, Sho Yamasaki, Spencer J. Williams
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Dylan G. M. Smith, Yuki Hosono, Masahiro Nagata, Sho Yamasaki, Spencer J. Williams
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Satvika Burugupalli, Catarina F. Almeida, Dylan G. M. Smith, Sayali Shah, Onisha Patel, Jamie Rossjohn, Adam P. Uldrich, Dale I. Godfrey, Spencer J. Williams