Solid-phase total synthesis and structural confirmation of antimicrobial longicatenamide A

• Takumi Matsumoto,
• Takefumi Kuranaga,
• Yuto Taniguchi,
• Weicheng Wang and
• Hideaki Kakeya

Beilstein J. Org. Chem. 2022, 18, 1560–1566, doi:10.3762/bjoc.18.166

• ], a solid-phase strategy can facilitate the production of a wider variety of analogous compounds than solution-phase synthesis [11]. Consequently, in this study, compound 1 was synthesized using a solid-phase strategy for future derivatization to produce probe molecules for deciphering microbial

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• to the Boc side chain protections. For the submonomer solution-phase synthesis of monomer 1 and oligomers 2–5, modifications from the standard synthesis conditions were required, notably for the substitution reaction. Thus, the first substitution reaction between benzyl bromoacetate and N-Boc-N

• describes for the first time the synthesis of peptoid oligomers consisting of consecutive N-alkylamino units, with the aim of creating peptoid oligomers with trans-amide linkages. For this first study, we focused on solution-phase synthesis of N-(methylamino)peptoids using a submonomer protocol and

• peptoids. (B) Atom labels in N-(methylamino)glycine monomers. Solution-phase synthesis of N-(methylamino)glycine oligomers using N-Boc-N-methylhydrazine as a submonomer. X-ray crystal structure of peptoid dimer 2: (A) single molecule; (B) unit cell, view along b axis (hydrogen atoms removed for clarity

Synthesis and bioactivity of pyrrole-conjugated phosphopeptides

• Qiuxin Zhang,
• Weiyi Tan and
• Bing Xu

Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17

• -phosphotyrosine, ʟ-phosphoserine, or ᴅ-phosphoserine, respectively. After being protected by an Fmoc group, these phosphorylated amino acids are suitable for solid-phase synthesis. We also used solution-phase synthesis to synthesize NBD-β-alanine according to the reported procedures [66]. We used standard Fmoc

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• ][98]. A detailed overview of the enzymatic strategies to generate artificial plant cell wall polymers was recently published [11][99]. Here, we describe the methods available to access well-defined XG oligo- and polysaccharides. The first solution phase synthesis of a nonasaccharide repeating unit was

• approach was efficient in solid phase as well as in solution phase synthesis. The participating (S)-(phenylthiomethyl) benzyl chiral auxiliary at the C-2 position of the glucosyl donor permitted the solid phase synthesis of a branched pentaglucan having a α(1–3) branch on an α(1–6) backbone [174]. Boron

• )-glucosamine macrocyclic compounds [265]. The iterative glycosylation of N-Phth protected 2-deoxy-2-aminothioglycosides allowed for the combinatorial synthesis of short oligoglucosamines having β(1–6) and/or β(1–4)-linkages [263]. Automated solution-phase synthesis of β(1–6)-glucosamine oligosaccharides

Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

• Alonso Pardo-Vargas,
• Priya Bharate,
• Martina Delbianco and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2019, 15, 2936–2940, doi:10.3762/bjoc.15.288

• chemical synthesis of AM is an attractive alternative. AM polysaccharides as large as 92-mers as well as many shorter AM oligomers have been prepared by solution-phase synthesis [16][17][18][19][20]. These multi-step syntheses are challenging and time-consuming. AGA reduces time and effort to access

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

• -bond formation in supramolecular chemistry which occurs in solution-phase synthesis is almost impossible in solid-state reactions. However, MacGillivray’s group demonstrated several examples of co-crystal formation or supramolecular synthesis in the solid phase through mechano-milling or dry grinding

Synthesis of the polyketide section of seragamide A and related cyclodepsipeptides via Negishi cross coupling

• Jan Hendrik Lang and
• Thomas Lindel

Beilstein J. Org. Chem. 2019, 15, 577–583, doi:10.3762/bjoc.15.53

• assembled by solution-phase synthesis and an open-chain analogue of the natural product was obtained. Keywords: jasplakinolide; marine natural products; Negishi coupling; polyketides; stereoselective synthesis; Introduction Our program on the synthesis of biologically active natural products with peptide

• to liberate the free carboxylic acid 29 and to couple it with the protected tripeptide 27 that was obtained by solution phase synthesis. We will now aim at the macrocyclisation of analogues of compound 31, which will probably require replacement of the bulky TIPS group installed at the threonine unit

Unexpected loss of stereoselectivity in glycosylation reactions during the synthesis of chondroitin sulfate oligosaccharides

• Teresa Mena-Barragán,
• José L. de Paz and
• Pedro M. Nieto

Beilstein J. Org. Chem. 2019, 15, 137–144, doi:10.3762/bjoc.15.14

• -phase synthesis, such as easy reaction monitoring by standard techniques and low consumption of donor building blocks to complete glycosylations. During the course of this investigation, unexpected stereochemical outcomes were observed in glycosylations involving glycosyl donors containing an N

• of a fluorous-assisted approach for the synthesis of CS oligosaccharides. The use of a fluorous tag allows the rapid isolation of fluorinated intermediates by performing a simple extraction from fluorous silica gel [27][28][29][30][31][32]. Moreover, this method maintains the advantages of solution

Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer

• Sagnik Sengupta,
• Mena Asha Krishnan,
• Premansh Dudhe,
• Ramesh B. Reddy,
• Bishnubasu Giri,
• Sudeshna Chattopadhyay and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2018, 14, 2665–2679, doi:10.3762/bjoc.14.244

• chain protecting moieties to introduce fluorescent tags. In addition to the above drawbacks, conventional methods for the synthesis of targeted fluorescent tagged bioconjugates [31] are a mixed approach of both solid and solution phase synthesis [32]. These involve several intermediary purification

Oligonucleotide analogues with cationic backbone linkages

• Melissa Meng and
• Christian Ducho

Beilstein J. Org. Chem. 2018, 14, 1293–1308, doi:10.3762/bjoc.14.111

• reported a solution-phase synthesis that enabled the formation of pentameric thymidinyl DNmt in the 3'→5' direction (reactions not shown) [68]. They then introduced an automated solid phase-supported synthesis which was compatible with standard techniques of DNA synthesis (Scheme 4) [69]. A derivative of 5

Preparation of trinucleotide phosphoramidites as synthons for the synthesis of gene libraries

• Ruth Suchsland,
• Bettina Appel and
• Sabine Müller

Beilstein J. Org. Chem. 2018, 14, 397–406, doi:10.3762/bjoc.14.28

• well suited to it. Also the solution-phase synthesis of protected trinucleotide building blocks has been described in the literature [21][22][23]. In an initial attempt, thymidine as a start nucleoside was tethered to a precipitative tetrapodal soluble support via a disulfide-linker [21] (Table 1

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

• Weizhun Yang,
• Bo Yang,
• Sherif Ramadan and
• Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

• glycosylated. This approach has been adapted to an automated solution-phase synthesis of poly-β-D-(1-6)-N-acetylglucosamine [78]. The aryl group in arylthioglycosides was first optimized for both the donor and the acceptor, where the electron-withdrawing fluorine on the phenyl ring gave the best result. The

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• reaction time, hazardous organic solvent, and tedious isolation procedure are implemented. Dekamin and co-workers have demonstrated the synthesis of pyrans using potassium phthalimide (POPI) as a catalyst under ball-milling which is found to be advantageous over solution phase synthesis [158]. Malonitrile

• have used KOH as base, neutral alumina as milling auxiliary. Both electron-donating and -withdrawing diazonium salts worked efficiently to give 70–90% of the products (Scheme 43) [171]. This solvent-free mechanomilling strategy reported to be superior to any solution phase synthesis because it avoids

• . Improvement in new synthetic methodologies under mechanomilling conditions with better results are always demanding, rather than “greening” the solution phase synthesis. Mechanochemical aldol condensation reactions [48]. Enantioselective organocatalyzed aldol reactions under mechanomilling. a) Based on binam

Synthesis of oligonucleotides on a soluble support

• Harri Lönnberg

Beilstein J. Org. Chem. 2017, 13, 1368–1387, doi:10.3762/bjoc.13.134

• to kilogram scale. In spite of this, solution-phase synthesis has received continuous interest, on one hand as a technique that could enable synthesis of even larger amounts and, on the other hand, as a gram scale laboratory synthesis without any special equipment. The synthesis on a soluble support

Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

• Yuta Isoda,
• Norihiko Sasaki,
• Kei Kitamura,
• Shuji Takahashi,
• Sujit Manmode,
• Naoko Takeda-Okuda,
• Jun-ichi Tamura,
• Toshiki Nokami and
• Toshiyuki Itoh

Beilstein J. Org. Chem. 2017, 13, 919–924, doi:10.3762/bjoc.13.93

• electrochemical solution-phase synthesis developed by us. The synthesis of structurally well-defined TMG-chitotriomycin has been accomplished in 10-steps from a disaccharide building block. Keywords: automated synthesis; electrochemical oxidation; glycosylation; glucosamine; total synthesis; Introduction

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

• Laszlo Jicsinszky,
• Marina Caporaso,
• Katia Martina,
• Emanuela Calcio Gaudino and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2016, 12, 2364–2371, doi:10.3762/bjoc.12.230

• solution phase synthesis of heptakis(6-deoxy-6-S-alkyl)-β-CDs is typical for the syntheses of intermediates of such compounds, however, their high lipophilicity means that isolation is not a technically trivial task. Scale up of the 1-dodecanethiol mechanochemical reaction (synthesis of compound 6, entry

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

• Darcy J. Atkinson,
• Briar J. Naysmith,
• Daniel P. Furkert and
• Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

• macrocyclic core of teixobactin by Reddy et al.: In 2016, Reddy et al. reported their synthetic efforts towards teixobactin (17) with a solution-phase synthesis of the macrocyclic core 109 (Scheme 24) [73]. Their synthetic approach focused on the macrolactonisation of a linear precursor 110 differing from

Preparation of a disulfide-linked precipitative soluble support for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks

• Amit M. Jabgunde,
• Alejandro Gimenez Molina,
• Pasi Virta and
• Harri Lönnberg

Beilstein J. Org. Chem. 2015, 11, 1553–1560, doi:10.3762/bjoc.11.171

• of a disulfide-tethered precipitative soluble support and its use for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks is described. To obtain the building blocks, N-acyl protected 2´-deoxy-5´-O-(4,4´-dimethoxytrityl)ribonucleosides were

Solution phase synthesis of short oligoribonucleotides on a precipitative tetrapodal support

• Alejandro Gimenez Molina,
• Amit M. Jabgunde,
• Pasi Virta and
• Harri Lönnberg

Beilstein J. Org. Chem. 2014, 10, 2279–2285, doi:10.3762/bjoc.10.237

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• procedure yields in very high purities of the final peptide, which surely would not have been possible by any other technique. In addition to solid and solution-phase synthesis, there are some other possibilities to produce these important molecules. Salmon calcitonin, human glucagon and human insulin are

Non-cross-linked polystyrene-supported 2-imidazolidinone chiral auxiliary: synthesis and application in asymmetric alkylation reactions

• Quynh Pham Bao Nguyen and
• Taek Hyeon Kim

Beilstein J. Org. Chem. 2013, 9, 2113–2119, doi:10.3762/bjoc.9.248

• solid phase and solution phase synthesis, non-cross-linked soluble polymer supports have attracted great interest because of some advantages such as high reactivity, easy analysis and purification of products [6][7][8][9][10][11][12]. Asymmetric alkylation reactions using polymer-supported chiral

From bead to flask: Synthesis of a complex β-amido-amide for probe-development studies

• Kevin S. Martin,
• Cristian Soldi,
• Kellan N. Candee,
• Hiromi I. Wettersten,
• Robert H. Weiss and
• Jared T. Shaw

Beilstein J. Org. Chem. 2013, 9, 260–264, doi:10.3762/bjoc.9.31

• completed a solution-phase synthesis of 1 and thus provided a common route to related compounds that may emerge from future on-bead screening experiments. The key step was the 3CR to form the β-amino acid core structure. Although the electronic requirements of this reaction limit it to electron-rich, or at

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

• the solid-phase synthesis of sialosides we undertook a model solution-phase synthesis of the glycan portion of GM3 ganglioside 16 (Scheme 2). GM3 serves as an important receptor for viral infection [24][25] and contains the common sialyl α-(2→3) galactose motif. The key step en route to compound 16

• carbamates has to be performed manually at the end of an automated sequence. These features make the automated platform very attractive for sialoside synthesis. Based on the encouraging results obtained for the solution-phase synthesis of 16, building blocks 4 and 5 were used for the automated solid-phase

• yield before hydrogenolysis gave the final trisaccharide 16 in 91% yield. The efficiency of the solid-phase and the solution-phase syntheses was compared. The solution-phase synthesis of trisaccharide 16 was completed with an overall yield of 42% (taking into account the preparation of compound 14, 69

Synthesis of trifunctional cyclo-β-tripeptide templates

• Frank Stein,
• Tahir Mehmood,
• Tilman Plass,
• Javid H. Zaidi and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2012, 8, 1576–1583, doi:10.3762/bjoc.8.180

• demanding due to solution-phase synthesis of the β-tripeptides and their final cyclization with low efficiency [8][9]. Moreover, only homofunctionalized cyclic β-tripeptides have been described so far [9][10]. To further investigate and exploit the potential of this class of circular peptides, a synthetic

Polyionic polymers – heterogeneous media for metal nanoparticles as catalyst in Suzuki–Miyaura and Heck–Mizoroki reactions under flow conditions

• Klaas Mennecke and
• Andreas Kirschning

Beilstein J. Org. Chem. 2009, 5, No. 21, doi:10.3762/bjoc.5.21

• processes creates an ideal setup for an automated solution-phase synthesis. Furthermore, this combination of enabling techniques has great potential in the production of fine chemicals [7][8]. In continuation of our efforts in developing immobilization concepts for reagents and catalysts including