A new synthetic protocol for coumarin amino acid

• Xinyi Xu,
• Xiaosong Hu and
• Jiangyun Wang

Beilstein J. Org. Chem. 2013, 9, 254–259, doi:10.3762/bjoc.9.30

• this approach, N-α-Cbz-L-glutamic acid α-benzyl ester was first converted into the side-chain β-keto ester and then it was reacted with resorcinol in methanesulfonic acid to afford 1a. The biggest shortcoming of this approach is that the purification of the final product requires a costly preparative

Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

• Rajendra Surasani,
• Dipak Kalita,
• A. V. Dhanunjaya Rao and
• K. B. Chandrasekhar

Beilstein J. Org. Chem. 2012, 8, 2004–2018, doi:10.3762/bjoc.8.227

• yield of the product in 3 h (Table 6, entry 4). The catalytic system developed by us for the coupling of amino acid esters with N-protected 7-azaindoles was ineffective for L-proline (6f), L-serine (6g), and L-glutamic acid (6h) (Table 6, entries 8–10). This may be ascribed to the fact that these amino

Synthesis of conformationally restricted glutamate and glutamine derivatives from carbonylation of orthopalladated phenylglycine derivatives

• Esteban P. Urriolabeitia,
• Eduardo Laga and
• Carlos Cativiela

Beilstein J. Org. Chem. 2012, 8, 1569–1575, doi:10.3762/bjoc.8.179

• )(CH(CO2Me)NMe2) (2a–j) (Nu = OR, NHR, NR2). Compounds 2a–j are conformationally restricted analogues of glutamic acid and glutamine and are interesting due to their biological and pharmacological properties. The reaction of [Pd(μ-Cl)(C6H4(CH(CO2Me)NHTf)-2)]2 (3) with nucleophiles in a CO atmosphere

• results, however, in the formation of the cyclic isoindolinone or the open 2-carboxyphenylglycine methyl esters, with the reaction outcome being driven by the choice of the solvent. Keywords: C–H functionalization; carbonylation; glutamic acid; glutamide; palladium; phenylglycine; Introduction The

• considered as glutamic acid derivatives, while 2g–j are analogues of glutamine, in which the β- and γ-positions belong to an aryl ring and display, therefore, a severe conformational restriction. The present method appears to be quite general, since it is valid for a wide range of alcohols and amines. In the

An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells

• Grazia Marano,
• Claas Gronewold,
• Martin Frank,
• Anette Merling,
• Christian Kliem,
• Sandra Sauer,
• Manfred Wiessler,
• Eva Frei and
• Reinhard Schwartz-Albiez

Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89

• glutamic acid–isoleucine–leucine–aspartic acid–valine (EILDV) is the binding motif of ligands of the α4β1 integrin. Both motifs are part of the amino acid sequence of fibronectin. In initial experiments we investigated the inhibition of cell adhesion to fibronectin with increasing concentrations of the RGD

Investigation of the network of preferred interactions in an artificial coiled-coil association using the peptide array technique

• Raheleh Rezaei Araghi,
• Carsten C. Mahrenholz,
• Rudolf Volkmer and
• Beate Koksch

Beilstein J. Org. Chem. 2012, 8, 640–649, doi:10.3762/bjoc.8.71

• preliminary structural investigation revealed that one such characteristic heptad can be substituted by a pentad repeat sequence of alternating β- and γ-amino acids, while retaining folding stability [18][19]. The backbone-engineered coiled-coil system comprises two peptides: A glutamic acid-rich α-poly

Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes

• Ricardo A. W. Neves Filho,
• Bernhard Westermann and
• Ludger A. Wessjohann

Beilstein J. Org. Chem. 2011, 7, 1504–1507, doi:10.3762/bjoc.7.175

• obtained through isolation from natural sources and the necessity to gain access to larger quantities of this substance for further biological screening, Silva and Joussef developed a straightforward total synthesis in six steps [14]. Starting from L-glutamic acid, their chiral-pool approach yielded the

Coupled chemo(enzymatic) reactions in continuous flow

• Ruslan Yuryev,
• Simon Strompen and
• Andreas Liese

Beilstein J. Org. Chem. 2011, 7, 1449–1467, doi:10.3762/bjoc.7.169

• tested in the continuous simultaneous synthesis of gluconic acid (9) and glutamic acid (8) by coupling the NADP+-dependent glucose (7) oxidation catalyzed by glucose oxidase with the reductive amination of α-ketoglutaric acid (6) catalyzed by glutamate dehydrogenase (Scheme 3). When the process was

• -(−)-Mandelic acid dehydrogenase; E2: Formate dehydrogenase [23]. Simultaneous synthesis of gluconic acid (9) and glutamic acid (8) in a continuously operated membrane reactor. E1: Glutamate dehydrogenase; E2: Glucose oxidase [24]. Production of L-tert-leucine (11) in a continuously operated enzyme membrane

A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky

• Guolei Zhao,
• Chao Yang,
• Bing Li and
• Wujiong Xia

Beilstein J. Org. Chem. 2011, 7, 1342–1346, doi:10.3762/bjoc.7.158

• -phenethyloctadecanamide (1), was isolated from the beetle Ambrostoma quadriimpressum Motschulsky. The structure of the amide was determined by NMR and MS. The absolute configuration of compound 1 was confirmed by an asymmetric total synthesis, which was started from L-glutamic acid. The construction of the aliphatic

• disconnected into two fragments, 2 and 3. The intermediate fragment 2 would be readily prepared from the commercially available ε-caprolactone. The crucial fragment 3 would be constructed from the intermediate 4 through Wittig olefination. The polyhydroxy compound 4 would be obtained from L-glutamic acid by

• selective protection. Our synthesis started from the ready available L-glutamic acid, as shown in Scheme 3. On the basis of the preceding literature [18][19][20], the hydroxy diester 5 was obtained in 35% yield (BnOH, H2SO4; NaNO2, AcOH; CH2N2). Protection of the secondary alcohol with the TBDPS group gave

Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan

• Axel G. Griesbeck,
• Jörg Neudörfl and
• Alan de Kiff

Beilstein J. Org. Chem. 2011, 7, 518–524, doi:10.3762/bjoc.7.60

•  1). For example, the glutamic acid derivative 3 resulted in the formation of a diastereoisomeric mixture of benzopyrrolizidinones 4 [6]. For a specific system, N-phthaloyl methionine (5), we have detected bielectrophoric behavior in that the electron transfer from the thioether group competes

An easy assembled fluorescent sensor for dicarboxylates and acidic amino acids

• Xiao-bo Zhou,
• Yuk-Wang Yip,
• Wing-Hong Chan and
• Albert W. M. Lee

Beilstein J. Org. Chem. 2011, 7, 75–81, doi:10.3762/bjoc.7.11

• solutions (5 mM) of the tetrabutylammonium salts of phthalatic acid, isophthalic acid, terephthalic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, D- and L-aspartic acid, and D- and L-glutamic acid in CH3CN were prepared. Stock solutions of hosts (1 mM) were prepared in DMSO. Test solutions

Catalysis: transition-state molecular recognition?

• Ian H. Williams

Beilstein J. Org. Chem. 2010, 6, 1026–1034, doi:10.3762/bjoc.6.117

• displacement mechanism involving a covalent glycosyl-enzyme intermediate. Formation and hydrolysis of this covalent intermediate occur via oxacarbenium ion-like TSs, with the assistance of two key active site glutamic acid residues [20]. Glu78 is deprotonated in the noncovalent enzyme-substrate reactant

Recent progress on the total synthesis of acetogenins from Annonaceae

• Nianguang Li,
• Zhihao Shi,
• Yuping Tang,
• Jianwei Chen and
• Xiang Li

Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48

• remained unknown. In 1998, Hanessian’s group [28] reported the stereocontrolled first total synthesis of a diastereomer of the presumed mono-THF type acetogenin annonacin A utilizing the “Chiron approach” (Scheme 4). The well-known lactone 30 obtained from L-glutamic acid was elaborated to a lactone

• intermediate 31; further manipulation and chain elongation at both ends of 31 produced an advanced intermediate 32. The anion of the phenyl sulfone 33, readily prepared from D-glutamic acid, was condensed directly with the ester function of 32 to give the α-keto sulfone 34, which was futher elaborated to ester

• solamin Solamin (57), a cytotoxic mono-tetrahydrofuranic γ-lactone acetogenin isolated from Annona muricata seeds in 1991 [38], was synthesized by Kitahara’s group in 1999 [39] through a direct coupling reaction (Scheme 8). The mono-THF unit 58, which was prepared from D-glutamic acid, was treated with

The first preparative solution phase synthesis of melanotan II

• Vladimir V. Ryakhovsky,
• Georgy A. Khachiyan,
• Nina F. Kosovova,
• Elena F. Isamiddinova and
• Andrey S. Ivanov

Beilstein J. Org. Chem. 2008, 4, No. 39, doi:10.3762/bjoc.4.39

• locking of the linear peptide sequence in its biologically active conformation by lactamization of the lysine ε-amino group and glutamic acid γ-carboxy group, led to a cyclic pseudopeptide analog of α-MSH with good metabolic stability and exceptional activity, known as melanotan II (2) (Figure 1). Results

Synthesis of (–)-Indolizidine 167B based on domino hydroformylation/cyclization reactions

• Giuditta Guazzelli,
• Raffaello Lazzaroni and
• Roberta Settambolo

Beilstein J. Org. Chem. 2008, 4, No. 2, doi:10.1186/1860-5397-4-2

• glutamic acid diethyl ester hydrochloride [9], to the corresponding 5,6-dihydroindolizine bearing the carboxyethyl group in position five. Successively a series of ester group transformations to n-propyl group followed by final exhaustive hydrogenation gave the desired product. In the synthesis of