Biosynthesis of rare hexoses using microorganisms and related enzymes

• Zijie Li,
• Yahui Gao,
• Hideki Nakanishi,
• Xiaodong Gao and
• Li Cai

Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281

• signaling, immunological recognition and host–pathogen interactions [63][64]. Gullapalli et al. demonstrated an effective way of obtaining deoxy L-fructose by combining chemical and biotechnological approaches (Scheme 10) [8]. Hydrogenation of 6-deoxy-L-mannose (L-rhamnose) produced 6-deoxy-L-mannitol (L

Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

• Felix Wojcik,
• Sinaida Lel,
• Alexander G. O’Brien,
• Peter H. Seeberger and
• Laura Hartmann

Beilstein J. Org. Chem. 2013, 9, 2395–2403, doi:10.3762/bjoc.9.276

• –protein receptor interactions play a key role for many events in glycobiology such as cell–cell or pathogen recognition [1]. Therefore, carbohydrate functionalization of non-natural materials such as polymers or dendrimers allows for bioactive materials that are used to modulate cellular behavior [1][2][3

Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O16

• Manas Jana and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 1757–1762, doi:10.3762/bjoc.9.203

• virulence property of the pathogen, several reports appeared in the past on the development of glycoconjugate based therapeutics against bacterial infections [10][11][12]. Detailed biological studies of the glycoconjugates require a significant quantity of the oligosaccharides, which is difficult to isolate

ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans

• Willmen Youngsaye,
• Cathy L. Hartland,
• Barbara J. Morgan,
• Amal Ting,
• Partha P. Nag,
• Benjamin Vincent,
• Carrie A. Mosher,
• Joshua A. Bittker,
• Sivaraman Dandapani,
• Michelle Palmer,
• Luke Whitesell,
• Susan Lindquist,
• Stuart L. Schreiber and
• Benito Munoz

Beilstein J. Org. Chem. 2013, 9, 1501–1507, doi:10.3762/bjoc.9.171

• a complementary approach that capitalizes upon the existing arsenal of antimicrobials to combat this medical dilemma [7][8][9][10]. By undermining the resistance mechanisms of the target pathogen, it is possible to restore efficacy to previously ineffective drugs thereby prolonging their status as

Synthesis and physicochemical characterization of novel phenotypic probes targeting the nuclear factor-kappa B signaling pathway

• Paul M. Hershberger,
• Satyamaheshwar Peddibhotla,
• E. Hampton Sessions,
• Daniela B. Divlianska,
• Ricardo G. Correa,
• Anthony B. Pinkerton,
• John C. Reed and
• Gregory P. Roth

Beilstein J. Org. Chem. 2013, 9, 900–907, doi:10.3762/bjoc.9.103

• oligomerization domain-1 (NOD1) inhibition (ML130 and ML146): The second program targeted proteins in the mammalian innate immune system that confer defense by detection of specific microbial ligands, or pathogen-associated molecular pattern microbial sensors known to house NOD1 (nucleotide-binding

De novo synthesis of D- and L-fucosamine containing disaccharides

• Daniele Leonori and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 332–341, doi:10.3762/bjoc.9.38

• bacteria Pseudomonas aeruginosa. P. aeruginosa is a nosocomial pathogen that is involved in ventilator-associated pneumonia and has become resistant to many antimicrobials. The somatic pili of P. aeruginosa are a major virulence factor playing a pivotal role in the adherence and invasiveness of the

• -linked glycan has been prepared and will be the basis for biological studies involving this pathogen. Experimental General experimental details All reagents were obtained from commercial suppliers and were used without further purification unless otherwise specified. All reactions were conducted under an

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

• Francesca Pertici,
• Norbert Varga,
• Arnoud van Duijn,
• Matias Rey-Carrizo,
• Anna Bernardi and
• Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

• obtained after deprotection of the alkyne moieties with K2CO3. Preliminary application As part of our program on bacterial adhesion inhibition by multivalent carbohydrates, the bacterial lectin LecA, a virulence factor of the problematic pathogen Pseudomonas aeruginosa is a target of interest [30][31

Synthesis of a derivative of α-D-Glcp(1->2)-D-Galf suitable for further glycosylation and of α-D-Glcp(1->2)-D-Gal, a disaccharide fragment obtained from varianose

• Carla Marino,
• Carlos Lima,
• Karina Mariño and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2012, 8, 2142–2148, doi:10.3762/bjoc.8.241

• ; glucosylgalactofuranose; glycosylaldonolactone; Penicillium varians; varianose; Introduction Carbohydrates are involved in a wide range of biological processes; they play important roles in host–pathogen interactions and in the immune response, where protein–glycan interactions mediate a variety of biological processes

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

• H. Bauke Albada,
• Alina-Iulia Chiriac,
• Michaela Wenzel,
• Maya Penkova,
• Julia E. Bandow,
• Hans-Georg Sahl and
• Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

• pathogens. Even if differences can be seen in the Gram-negative values, none of the RW-peptides was very active. Unfortunately, none of the peptides showed significant activity against Pseudomonas aeruginosa, a prominent pathogen that causes infections in e.g., cystic fibrosis patients. However, activities

Automated synthesis of sialylated oligosaccharides

• Davide Esposito,
• Mattan Hurevich,
• Bastien Castagner,
• Cheng-Chung Wang and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183

• ; sialosides; Introduction Sialic acid (Sia) belongs to a family of nonulosonic acids, i.e., monosaccharides equipped with a carboxylic moiety and a nine-carbon backbone, which play a unique role in glycobiology. Sia-containing glycans mediate pathogen invasion [1] and are involved in signalling cascades

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• in GlyAffinity. PACDB (Pathogen Adherence Carbohydrate Database) lists glycan-binding proteins that are involved in the adherence of pathogens to the host. The data are extracted from the literature and can be accessed by pathogen names or by related diseases. Integration of carbohydrate databases It

• challenge for glycoinformatics, but it also offers many possibilities to synthesize carbohydrates or glycomimetics that target specific pathogen proteins. For example, oligosaccharide motifs that are found in surface carbohydrates of pathogens, but not in host organisms or in symbiotes, can serve as

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

• Henning S. G. Beckmann,
• Heiko M. Möller and
• Valentin Wittmann

Beilstein J. Org. Chem. 2012, 8, 819–826, doi:10.3762/bjoc.8.91

• ; cluster effect; lectins; multivalency; Introduction The recognition of carbohydrate structures by carbohydrate binding proteins (lectins) plays a fundamental role in numerous intra- and intercellular events during development, inflammation, immune response, cancer metastasis, and pathogen–host

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• infection to progress. As a consequence, mutations of the pathogen adhesion proteins, resulting in a loss of cell-surface binding recognition are not very likely to occur. Interference with the microbe binding events by employing an anti-adhesive strategy could therefore be very efficient. In several

• monosaccharide ligands have been prepared and evaluated [123]. The type 1 fimbriated Echerichia coli is a pathogen responsible for urinary tract infections with millions of cases every year [124]. The type 1 fimbriae have been identified to be a major contributor to these infections [125][126]. The FimH lectin

• distance (Figure 2) [140][141][142]. In another study, a combinatorial library of fucosyl-peptide dendrimers was synthesized and screened for binding to the fucose-specific lectin (LecB) from Pseudomonas aeruginosa, a pathogen causing severe infections in patients leading to chronic inflammation in the

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

• Baptiste Thomas,
• Michele Fiore,
• Isabelle Bossu,
• Pascal Dumy and
• Olivier Renaudet

Beilstein J. Org. Chem. 2012, 8, 421–427, doi:10.3762/bjoc.8.47

• : chemoselective ligation; click chemistry; cyclopeptide; heteroglycocluster; oxime; Introduction Multivalent interactions between carbohydrates and proteins play key roles in diverse biological events, including fertilization, cell–cell communication, host–pathogen interactions, immune response and cancer

Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9

• Abhishek Santra and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2011, 7, 1182–1188, doi:10.3762/bjoc.7.137

• that cause diarrhoeal disease and dysentery (e.g., shigellosis). Among several types of Shigella species, Shigella dysenteriae is the most virulent pathogen causing devastating health problems in developing countries [1][2][3]. Shigella strains are classified into four species: Shigella boydii

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• worldwide [37][38]. IFIs are characterized by high morbidity and mortality and are difficult to diagnose, prevent and treat. In the USA, Candida spp. is the fourth most common nosocomial pathogen with the highest crude mortality rate (40%) [39]. In addition to Aspergillus spp., new and emerging fungal

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• agent of tuberculosis (TB), possesses a complex cell wall containing mannose-rich glycophospholids termed phosphatidylinositol mannosides (PIMs), lipomannan (LM), and lipoarabinomannan (LAM). These glycophospholipids play important roles in cell wall function and host–pathogen interactions. Synthetic

• , and LAM [8]. Through studies with gene deletion mutants of mycobacterial strains, several steps in the biosynthesis of the PIMs, LM and LAM have been shown to be essential for bacterial survival and it is now well appreciated that they are crucial cell-surface molecules that mediate host–pathogen

• development of glycomimetic compounds. Homogeneous synthetic substructures have been used to deconvolute aspects of substrate recognition by biosynthetic enzymes and the structural determinants of host–pathogen interactions including antibody recognition and immune pattern-recognition systems such as the