Synthesis and characterization of water-soluble C₆₀–peptide conjugates

• Yue Ma,
• Lorenzo Persi and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

• on resin, a GABA residue was attached to the N-terminus of the peptide in order to provide a less-hindered primary amine, enabling an efficient amide conjugation reaction with biscarboxylic acid-substituted C60 derivative 3. Compound 3 was prepared by Prato reaction of C60 and an N-glycine derivative

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• platyphylla (BRAPP), Bromus tectorum (BROTE), Echinochloa crus-galli (ECHCG), Digitaria sanguinalis (DIGSA), Eleusine indica (ELEIN), Glycine max (GLXMA), Lolium rigidum (LOLRI), Lolium sp. (LOLSS), resistant Lolium sp. (LOLSS_R, origin: France), Poa annua (POAAN), Setaria viridis (SETVI), Sorghum halepense

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• : A1-type AMYs can be generated from the condensation of aldehydes with α- and N-dialkylglycine esters, A2-type AMYs are derived from α-alkylglycine esters, A3-type AMYs are derived from N-alkylglycine esters, and A4-type AMYs are derived from glycine esters. Stabilized zwitterions A1–A4 have the

• condensation of N-dialkylglycines [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51]. The N–H-type semi-stabilized AMYs B3 are generated through decarboxylative condensation of arylaldehydes with α-alkylglycines, while B4-type AMYs are derived from the reaction of glycine [52][53][54][55

• ketones can result in a different kind of AMYs to address the issue. The reaction of trifluoromethyl ketones with glycine or α-substituted amino acids generated stabilized AMY 8 which underwent cycloaddition with maleimides to give 2-CF3-substituted pyrrolidines 9 in 50–76% yield (Scheme 5) [65]. Both the

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp³)–H to construct C–C bonds

• Hui Yu and
• Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

• , and TBHP acting as both an oxidant and a radical initiator. In 2015, Wang et al. reported the synthesis of quinoline lactones by the double oxidative dehydrogenation (DOD) reaction between glycine derivatives and tetrahydrofuran using the FeCl2/HCl/TBHP system (Scheme 19) [80]. This practical coupling

• unique catalytic behavior [89]. However, there are only a few examples of cobalt catalysis in CDC reactions. Limited by the activity of Co catalysts, there are few examples of Co-catalyzed reactions involving ether C(sp3)–H bond activation. The Co-catalyzed C(sp3)–C(sp3) CDC of glycine and peptide

• derivatives with THF was developed by Correa et al. (Scheme 28) [90]. This study presents a cost-effective cobalt-catalyzed C(sp3)–H functionalization strategy for α-aminocarbonyl compounds. The method allows for the direct introduction of ethers into a diverse range of glycine derivatives. Importantly, the

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

• Alena V. Dmitrieva,
• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

• )-1-benzylpyrrolidine-2-carboxamide) and its Ni(II)–Schiff base complexes formed of glycine, serine, and dehydroalanine are reported. A bulky tert-butyl substituent in the phenylene fragment precludes unwanted oxidative dimerization of the Schiff base complex, making it suitable for targeted

• thermodynamically controlled stereoselectivity as compared to the parent Belokon complex. Additionally, functionalization with the tert-butyl group significantly enhances the reactivity of the deprotonated glycine complex towards electrophiles as compared to the anionic species formed from the original Belokon

• employing chiral auxiliaries [4][5] and asymmetric phase-transfer catalysis [6][7]. The former approach is commonly based on the application of chiral derivatives of glycine containing structurally diverse chiral auxiliaries, both cyclic [8][9][10][11] and acyclic [12][13]. Transition-metal complexes

Synthesis of (−)-halichonic acid and (−)-halichonic acid B

• Keith P. Reber and
• Emma L. Niner

Beilstein J. Org. Chem. 2022, 18, 1629–1635, doi:10.3762/bjoc.18.174

• derived from a common biosynthetic pathway starting from farnesyl pyrophosphate and glycine [5]. This prompted us to investigate a biomimetic synthesis in which the halichonic acids could be prepared from a common imine intermediate via divergent intramolecular aza-Prins cyclizations [8]. Herein, we

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

• ] and provides insights into the biosynthesis pathways of these peptides [14]. However, the biosynthetic gene clusters of compounds 1–4 remain unidentified. Therefore, the least sterically hindered amine, namely the amino group of glycine, was selected as a nucleophile of the cyclization reaction in

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

• Oleg A. Levitskiy,
• Olga I. Aglamazova,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121

• electrochemical three-membered ring opening, a voltammetric study was performed. As it has been shown in our previous publications [49][50][51], the electrochemical behavior and the orbitals location sites are dependent on the type of the amino acid involved in the Schiff base complex. The LUMOs of the glycine

• significant bathochromic shift as compared to the deprotonated glycine complex (λmax = 458 nm [9]) indicates an elongation of the conjugation chain and formation of the anionic complex which can be considered as a vinylog of the parent glycine derivative (Scheme 2) The anionic species formed in the

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

• presence of sodium hydride in dioxane, affording tricyclic γ-phosphonolactams 74, 78, and 81 in low to moderate yields (Scheme 14) [34]. In 2005, Aladzheva and co-workers prepared γ-phosphonolactams 85 from the substitution of ethyl 2-(3-chloropropyl)aminoalkanoates 82 derived from glycine and ᴅʟ-alanine

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

• -(alkylamino)glycine units is investigated. We demonstrate that N-(methylamino)glycine homooligomers can be readily synthesized in solution using N-Boc-N-methylhydrazine as a peptoid submonomer and stepwise or segment coupling methodologies. Their structures were analyzed in solution by 1D and 2D NMR, in the

• , however, the N-alkylamino-containing glycine units were not introduced consecutively but every two or three residues. We describe here the synthesis and study of the first representatives of peptoids containing exclusively N-alkylamino-substituted amides. As the first representatives of this family we

• concentration range of 2–50 mM for monomer A in CDCl3 (Δδ = 3.09 ppm, Supporting Information File 1, Figure S1), suggesting intermolecular hydrogen bonding, in sharp contrast to the Δδ = 0.01 ppm measured for the piperidinyl amide-capped N-benzylamino glycine monomer B, which is further characterized by a

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Synthesis and late stage modifications of Cyl derivatives

• Phil Servatius and
• Uli Kazmaier

Beilstein J. Org. Chem. 2022, 18, 174–181, doi:10.3762/bjoc.18.19

• suitable protected linear precursor A (Scheme 2, PG: protecting group), the resulting carboxylic acid obtained can directly be activated and subjected to cyclization. If the glycine allyl ester is incorporated as the last building block into the C-terminus of the peptide, this concept should provide a high

• approach, 1 was mono-O-allylated to 2 under similar conditions reported previously for monobenzylation (Scheme 3) [50]. Iodination (3) and subsequent elimination of the iodide with zinc dust gave allylic alcohol 4 as a single enantiomer, which was esterified with Boc-protected glycine to allyl ester 5

• the peptide can have a significant effect on the Claisen rearrangement and therefore we synthesized the Cbz- as well as the Boc-protected peptides 8a and 8b. The tripeptide building blocks were previously also used in the Cyl-1 synthesis. Glycine allyl ester 5 was Boc-deprotected to give amine 7 as

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

• . According to this rationale, replacing the Nap capping group in 1 with a dipyrrole or a tripyrrole segment at the N-terminal generates 2a and 2b. Introducing two or three glycine residues between the pyrrole segment and the self-assembling segment produces 2c–h, which would help to understand the role of a

• . Switching the ᴅ-phosphoserine in 4a and 4b by ʟ-phosphoserine (pS), creates 5a and 5b. ᴅ-Trialanine replaces triglycine in 2f–h to produce 6a–c, which should resist to proteases, such as polyglycine hydrolases [73], which are known to cleave at the glycine–glycine site. The addition of an arginine residue

• the sidechain of NBD-ffky or NBD-ffkpy [66], another previously studied self-assembling peptide, produces 13 and 14. In addition, 15a–c consist of only pyrrole and glycine units, which should help delineate the roles of the self-assembling motif and the enzymatic triggers. Synthesis The synthesis of

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• reaction probably occurs in the o-quinone moiety group. Subsequently, Obo [46] demonstrated that the reaction of β-NQSNa (18) and glycine ethyl ester form 19 in a 46% yield, indicating that the reaction occurred at C4 (Scheme 2). Fu and co-workers [47] prepared a new electrochemical sensor for the specific

• recognition of cholylglycine, which is a combination of cholic acid and glycine. The β-cyclodextrin/graphene oxide composite forms an inclusion complex with a β-NQS guest. The amino group of cholylglycine can bind to β-NQS by a nucleophilic substitution reaction, resulting in a decrease in the electrochemical

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Targeting active site residues and structural anchoring positions in terpene synthases

• Anwei Hou and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 2441–2449, doi:10.3762/bjoc.17.161

• glycine is observed in the corresponding position (G180). Furthermore, the highly conserved Asn located eight positions downstream of the NSE triad [15] is in SmTS1 substituted by an Arg (R242). A usually conserved Trp six positions upstream of the C-terminal RY pair [23], that is itself involved in

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines

• Zara M. Seibel,
• Jeffrey S. Bandar and
• Tristan H. Lambert

Beilstein J. Org. Chem. 2021, 17, 2077–2084, doi:10.3762/bjoc.17.134

• strategy for the enanantioselective conjugate addition of amino acid derivatives for this reaction remains an unmet goal. Our group previously described a chiral cyclopropenimine catalyst that displayed outstanding reactivity for addition reactions of glycine imines [40][41]. We hypothesized that this

• the reaction (Table 2, entry 12), the incorporation of this substituent led to a nearly total loss in selectivity. Although we have not examined this specific reaction computationally, it is reasonable to expect that it shares many similarities to the corresponding glycine imine addition we previously

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

• Mathias B. Danielsen and
• Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

• relative to the downregulation of the reference ASO (Oblimersen) [91]. In an entirely different approach, the 2’-amino group of amino-LNA-thymine (amino-LNA-T) has been explored as an attachment point for various cationic groups. As one example, amino acids such as glycine, lysine, and proline in different

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

• positions of the backbone α-Modified PNA: Adding substituents to the N-(2-aminoethyl)glycine backbone has been an obvious starting point for PNA modification. Nielsen and co-workers were the first to replace the glycine residues in PNA backbone with various chiral amino acids [67][68]. Most of these α

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• of Technology Indore, Khandwa Road, Simrol, Indore-453 552, India, School of Chemical Sciences, National Institute of Science Education and Research, Bhubaneswar-752 050, Odisha, India 10.3762/bjoc.17.101 Abstract 1,5-Disubstituted indole-2-carboxaldehyde derivatives 1a–h and glycine alkyl esters 2a

• the literature, there is only a limited number of direct synthetic procedures to prepare γ-carbolines till date [28], and this gives a cutting edge advantage to our new protocol wherein a solvent and metal-free direct access to the γ-carboline core from substituted indole-2-aldehyes and glycine ester

• . Herein, we report an interesting observation for conversion of substituted indole-2-aldehydes 1 to 1-indolyl-3,5,8-substituted γ-carbolines 3 by a cascade imination-heterocylization pathway when treated with the salt glycine methyl ester hydrochloride (2a) in the presence of a base. Earlier in the

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

• Zhonglie Yang,
• Yutong Liu,
• Kun Cao,
• Xiaobin Zhang,
• Hezhong Jiang and
• Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

• ] developed a visible-light-induced [3 + 2] cycloaddition reaction between glycine derivatives 57 and aryl epoxides 58, which can efficiently prepare a series of multisubstituted 1,3-oxazolidines 59 at room temperature (Scheme 20). The strategy can be applied smoothly to an extensive range of glycine

• -functionalization of glycine derivatives. The construction of C–C bonds As a crucial element in the construction of various organic scaffolds, the formation of C–C bonds remains a hot topic in the field of synthetic organic chemistry. The conventional approaches of C–C-bond construction typically employ transition

• absorption of EDA complex in the visible-light region. In 2020, Xu and colleagues [39] proposed a visible-light-promoted alkylation reaction using Katritzky salts such as 128 and glycine derivative 127 (or glycine segments in peptides) initiated by an EDA complex. This successfully realized the simple

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• given in Scheme 9 [87]. On this pathway for the synthesis of conjugates 19 and 20, acid 18 is cross-linked with a peptide component using a milder carbodiimide method via the starting methanofullerene 17. Similar to Scheme 8, fullerene adducts 21 and 22 with glycine and phenylalanine, respectively, were

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

• 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

• proposed for the preparation of functional drug carriers for clinical applications [25][28][29]. In order to alleviate the steric hindrance effect of PEG chains, a novel spacer consisting of alternating serine–glycine sequences (SG)n was introduced between the ligand and lipid within the molecular

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• -aminophosphonodichloride 92 with phenol and methyl (S)-2-hydroxypentanoate (18). All synthetic phosphonodepsipeptides 99, 102, and 104 were considered as glutathione-analogue phosphonopeptides as mechanism-based inhibitors of γ-glutamyl transpeptidase for probing the cysteinyl-glycine binding site (Scheme 16) [31