Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• -product biosynthesis and combinatorial solid-phase chemistry, this strategy has expanded the sequence space of macrocyclic peptides significantly (Scheme 2c). The daptomycins The calcium-dependent antibiotic (CDA, 11), daptomycin (12), and A54145 are acidic lipopeptides isolated from Streptomycetes, which

• biosynthesis of these acidic lipopeptides, Marahiel and co-workers accomplished a chemoenzymatic synthesis of the calcium-dependent antibiotic (CDA,11) utilizing CDA3 TE, a cyclase derived from CDA synthetase [53]. To simulate the native peptide-S-PCP substrate, they evaluated four leaving groups: SNAC

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• neglected parasite. In the presence of RAW 264.7 cell lines, compound 1 was particularly selective towards Leishmania donovani (Laveran and Mesnil) Ross (D10) with an SI value of 14.71. The bioactivity studies conducted confirm the role of these cyclic lipopeptides as defense chemicals in their natural

• environment and their ability to be biologically active across different species. Keywords: Leishmania; lipopeptides; molecular networking; sequence tagging; trypanosomes; Introduction Microbes belonging to the genus Bacillus are mainly Gram-positive with only a few examples characterized as Gram-negative

• examine similar lipopeptide structures previously characterized in the literature that possessed both the fatty acid chain terminating as an isopropyl and adjacent to Glu residue connected by an amide bond. This detailed examination revealed that in the structure of these cyclic lipopeptides, the

First total synthesis of hoshinoamide A

• Haipin Zhou,
• Zihan Rui,
• Yiming Yang,
• Shengtao Xu,
• Yutian Shao and
• Long Liu

Beilstein J. Org. Chem. 2021, 17, 2924–2931, doi:10.3762/bjoc.17.201

• 210009, China Taizhou Medical Hi-Tech Development Public Services Platform, Taizhou 225300, China 10.3762/bjoc.17.201 Abstract Hoshinoamides A, B and C, linear lipopeptides, were isolated from the marine cyanobacterium Caldora penicillata, with potent antiplasmodial activity against chloroquine

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• Millipore, USA), providing the final LNP–DNA lipoplexes in 1× PBS pH 7.4 (3 mg/mL final lipid concentration). Postinsertion of peptides was carried out by diluting the peptides to a final concentration of 1.7 µg/mL Tat lipid and 3.0 µg/mL T7 lipid in 1× PBS pH 7.4. Thereafter, diluted lipopeptides (18 µL T7

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

• Masayori Hagimori,
• Estefanía E. Mendoza-Ortega and
• Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

• Graduate School of Biomedical Sciences, Nagasaki University, 1-7-1 Sakamoto, Nagasaki 852-8501, Japan 10.3762/bjoc.17.45 Abstract Ligand-targeted microbubbles are focusing interest for molecular imaging and delivery of chemotherapeutics. Lipid–peptide conjugates (lipopeptides) that feature alternating

• serine–glycine (SG)n segments rather than classical poly(oxyethylene) linkers between the lipid polar head and a targeting ligand were proposed for the liposome-mediated, selective delivery of anticancer drugs. Here, we report the synthesis of perfluoroalkylated lipopeptides (F-lipopeptides) bearing two

• hydrophobic chains (CnF2n+1, n = 6, 7, 8, 1–3) grafted through a lysine moiety on a hydrophilic chain composed of a lysine–serine–serine (KSS) sequence followed by 5 SG sequences. These F-lipopeptides are precursors of targeting lipopeptide conjugates. A hydrocarbon counterpart with a C10H21 chain (4) was

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

A new member of the fusaricidin family – structure elucidation and synthesis of fusaricidin E

• Marcel Reimann,
• Louis P. Sandjo,
• Luis Antelo,
• Eckhard Thines,
• Isabella Siepe and
• Till Opatz

Beilstein J. Org. Chem. 2017, 13, 1430–1438, doi:10.3762/bjoc.13.140

• structure and the suggested stereochemistry. The synthesis was based on a new strategy which includes an efficient access to the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain from erucamide. Keywords: cyclodepsipeptides; fusaricidins; lipopeptides; structure elucidation; total synthesis

Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

• Vincent Fagan,
• Istvan Toth and
• Pavla Simerska

Beilstein J. Org. Chem. 2014, 10, 1741–1748, doi:10.3762/bjoc.10.181

• analytical HPLC (Supporting Information File 1). Conclusion A concise and convenient synthesis of a versatile carbohydrate building block was devised. A very efficient procedure for the lipidation of Fmoc-lysine is reported, which may find widespread application for the preparation of lipopeptides. Using

A practical synthesis of long-chain iso-fatty acids (iso-C₁₂–C₁₉) and related natural products

• Mark B. Richardson and
• Spencer J. Williams

Beilstein J. Org. Chem. 2013, 9, 1807–1812, doi:10.3762/bjoc.9.210

• amides in natural products including septacidin [3], teicoplanins [4], tunicaminyluracil-based antibiotics [5] (tunicamycins [6], corynetoxins [7], and streptovirudins [8]), the arylomycin glycopeptide antibiotics [9][10], maradolipids [11], plipastatin-type lipopeptides [12], Nod factors [13

2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β²-amino acids

• Markus Nahrwold,
• Arvydas Stončius,
• Anna Penner,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43

• ]. Examples are cryptophycin-1 (a highly cytotoxic depsipeptide produced by cyanobacteria Nostoc sp. GSV224 and ATCC53789) [11][12][13][14] as well as a class of lipopeptides isolated from various fungi, comprising topostatin (a topoisomerase I and II inhibitor) [15], YM-170320 (an inhibitor of ergosterol