Search results

Search for "serine" in Full Text gives 137 result(s) in Beilstein Journal of Organic Chemistry.

p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates

  • Madhuri Vangala and
  • Ganesh P Shinde

Beilstein J. Org. Chem. 2016, 12, 2086–2092, doi:10.3762/bjoc.12.197

Graphical Abstract
  • containing substrates such as the p-nitrophenyl carbonate of 9-fluorenemethanol 16a and N-Cbz-L-serine methyl ester 17a, resulted in the dibenzofulvene product 16b in the former, and a mixture of products in the latter, with DBN acting as a base. Even though the γ-lactam products were the only major
PDF
Album
Supp Info
Full Research Paper
Published 26 Sep 2016

Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

  • Pramod R. Markad,
  • Navanath Kumbhar and
  • Dilip D. Dhavale

Beilstein J. Org. Chem. 2016, 12, 1765–1771, doi:10.3762/bjoc.12.165

Graphical Abstract
  • D-serine as a starting material [6]. In this regard, our group has recently reported the synthesis of the C3’-branched carbohydrate core of amipurimycin starting from D-glucose [15]. In the continuation of this area, we now report the synthesis of the amipurimycin pyranose core comprising of (a) a
PDF
Album
Supp Info
Full Research Paper
Published 05 Aug 2016

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

  • Mei-Yuan Hsu,
  • Yi-Pei Liu,
  • Sarah Lam,
  • Su-Ching Lin and
  • Cheng-Chung Wang

Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164

Graphical Abstract
  • -butanol (16), 5-azidopentanol (17), cyclohexanol (18) and 2-adamantanol (19), to give O-2-deoxyglucosides in high yields (74–90%) and α-selectivities (α:β = 7–10:1, Table 3, entries 2–8). Regarding the glycosylation with amino acid derivatives, L-serine 20 and threonine derivative 21, increased ratio of β
  • -Serine and threonine derivatives 20 and 21 reacted with galactal 4 to give the glycosylated amino acids 59 and 60 (Table 4, entries 9 and 10) in excellent selectivities (59, α only; 60, α:β = 9:1) but in different yields (59, 50%; 60, 97%). In Table 4, entry 11, disaccharide 61 was acquired in the
PDF
Album
Supp Info
Full Research Paper
Published 04 Aug 2016

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

  • Franziska Hemmerling and
  • Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

Graphical Abstract
PDF
Album
Review
Published 20 Jul 2016

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

  • Andrew W. Truman

Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120

Graphical Abstract
  • -translationally modified into the final product, and a heterotrimeric complex that is responsible for both heterocyclisation of serine and cysteine residues, and subsequent oxidation of (ox/thi)azolines into (ox/thi)azoles (Figure 3A). This catalytic complex consists of “C” and “D” proteins (annotated as McbB and
  • McbD, respectively, for microcin B17) that cooperate to catalyse heterocyclisation of specific serine and cysteine residues in McbA, and a flavin-dependent dehydrogenase (the “B-protein”, McbC for microcin B17) that oxidises these heterocycles. These early in vitro studies indicated that the “C-protein
  • then be attacked by an adjacent serine or cysteine side chain, thus releasing phosphate/AMP and generating the heterocycle. This order of steps was not advocated by either the Naismith or Mitchell groups as it requires a disfavoured 5-endo-trig cyclisation, although this mode of cyclisation is
PDF
Album
Review
Published 20 Jun 2016

NeoPHOX – a structurally tunable ligand system for asymmetric catalysis

  • Jaroslav Padevět,
  • Marcus G. Schrems,
  • Robin Scheil and
  • Andreas Pfaltz

Beilstein J. Org. Chem. 2016, 12, 1185–1195, doi:10.3762/bjoc.12.114

Graphical Abstract
  • Jaroslav Padevet Marcus G. Schrems Robin Scheil Andreas Pfaltz Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland 10.3762/bjoc.12.114 Abstract A synthesis of new NeoPHOX ligands derived from serine or threonine has been developed. The central
  • the substantially higher ee values induced by the analogous catalyst Ir-1a [28] lacking substituents at C(5). Based on these negative results we chose a new approach based on serine or threonine as starting materials (Figure 4). The carboxyl group of these amino acids serves as surrogate for the tert
  • protecting group, the steric properties of the ligand can be optimized for a specific application. PHOX ligands of this type have been previously prepared from serine and successfully used in iridium-catalyzed hydrogenation [29][30]. Synthesis of serine- and threonine-derived NeoPHOX ligands The synthesis
PDF
Album
Supp Info
Full Research Paper
Published 13 Jun 2016

One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters

  • Gastón Silveira-Dorta,
  • Sergio J. Álvarez-Méndez,
  • Víctor S. Martín and
  • José M. Padrón

Beilstein J. Org. Chem. 2016, 12, 957–962, doi:10.3762/bjoc.12.94

Graphical Abstract
  • better Z-(dia)stereoselectivity was observed when compared to the previous one-pot method. The (dia)stereoselectivity of the process was affected neither by the reaction solvent nor by the amount of DIBAL-H employed. The method is compatible with the presence of free hydroxy groups as shown with serine
  • -protected α-amino esters requires three chemical steps, i.e. reduction, oxidation and olefination (Figure 1) [9][10]. When the benzyl group is used as protecting group for the nitrogen functionality, the method represents a variation of the well-known Reetz protocol [11]. In the particular case of serine
  • aldehydes. It comprises the one-pot sequential reduction to aldehyde with DIBAL-H at −78 °C and subsequent in situ addition of Grignard reagents. Remarkably, our method is friendly with serine and threonine derivatives without the requisite to protect the β-hydroxy group. With this tool in hand, we thought
PDF
Album
Supp Info
Full Research Paper
Published 12 May 2016

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

  • Daniel Wiegmann,
  • Stefan Koppermann,
  • Marius Wirth,
  • Giuliana Niro,
  • Kristin Leyerer and
  • Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

Graphical Abstract
  • . synthesised the hydroxyleucine moiety found in naturally occurring muraymycins of classes A to C (Scheme 8) [107]. Adapting a strategy developed by Zhu et al., D-serine (59) was stereoselectively converted into the protected amino alcohol 60 [108]. Key intermediate 60 was then Cbz- and acetonide protected to
PDF
Album
Review
Published 22 Apr 2016

Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

  • Gergely L. Tolnai,
  • Jonathan P. Brand and
  • Jerome Waser

Beilstein J. Org. Chem. 2016, 12, 745–749, doi:10.3762/bjoc.12.74

Graphical Abstract
  • under mild conditions and could be applied to peptides containing other nucleophilic and aromatic amino acids, such as serine, phenylalanine or tyrosine. Keywords: alkynes; C–H functionalization; gold catalysis; hypervalent iodine; peptides; Introduction Alkynes have always been important building
  • other aromatic amino acids, such as phenylalanine or tyrosine (products 5c and 5d). Serine and proline containing dipeptides 5e and 5f could also be obtained in 64% and 53% yield, respectively. The reaction was therefore general for dipeptides bearing tryptophan at the C-terminus. On the other hand
PDF
Album
Supp Info
Letter
Published 19 Apr 2016

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

  • Guozheng Huang,
  • Simon Schramm,
  • Jörg Heilmann,
  • David Biedermann,
  • Vladimír Křen and
  • Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

Graphical Abstract
  • alcohols and bulky acids: Cherney and Wang observed an elimination of a serine derivative during esterification experiments [23]. During conversion of substituted benzyl alcohols to amines under Mitsunobu conditions, elimination also occurred [24]. Dehydration under Mitsunobu conditions has been applied in
PDF
Album
Supp Info
Full Research Paper
Published 08 Apr 2016

Antibiotics from predatory bacteria

  • Juliane Korp,
  • María S. Vela Gurovic and
  • Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

Graphical Abstract
  • , requires a tight regulatory network in predatory myxobacteria [80]. This is also reflected in the genome of M. xanthus DK1622, which features an unusual high duplication frequency of genes encoding regulatory proteins like serine-threonine kinases and enhancer binding proteins (EBPs) [43]. EBPs are
PDF
Album
Review
Published 30 Mar 2016

Natural products from microbes associated with insects

  • Christine Beemelmanns,
  • Huijuan Guo,
  • Maja Rischer and
  • Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

Graphical Abstract
  • D-serine. Due to the presence in conidia, serinocyclines have also been hypothesized to play a role in the virulence of M. anisopliae. Chemical analysis of the entomopathogenic fungus B. bassiana yielded beauvericin (43), a depsipeptide with alternating methylphenylalanyl and hydroxyisovaleryl
PDF
Album
Review
Published 19 Feb 2016

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

  • Louis P. Sandjo,
  • Victor Kuete and
  • Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

Graphical Abstract
  • phosphatase B (PtpB) [31] and serine protease [32]. The focus of this review is on pyridoacridine-related metabolites as one of the many interesting groups of alkaloids produced from marine sources. They are generally produced by marine sponges, ascidians [33] and tunicates [34] and they are structurally
PDF
Album
Review
Published 18 Sep 2015

Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds

  • Michaela Mühlberg,
  • Michael G. Hoesl,
  • Christian Kuehne,
  • Jens Dernedde,
  • Nediljko Budisa and
  • Christian P. R. Hackenberger

Beilstein J. Org. Chem. 2015, 11, 784–791, doi:10.3762/bjoc.11.88

Graphical Abstract
  • amino acids like glycine, alanine or serine in the native process of N-terminal methionine excision (NME) [43]. This process exposes Ser2 at the N-terminus for subsequent N-terminal oxime ligation. It has to be noted that the incorporation of Aha, as known [42][44], can hamper NME and therefore delivers
PDF
Album
Supp Info
Full Research Paper
Published 13 May 2015

Regulation of integrin and growth factor signaling in biomaterials for osteodifferentiation

  • Qiang Wei,
  • Theresa L. M. Pohl,
  • Anja Seckinger,
  • Joachim P. Spatz and
  • Elisabetta A. Cavalcanti-Adam

Beilstein J. Org. Chem. 2015, 11, 773–783, doi:10.3762/bjoc.11.87

Graphical Abstract
  • higher bioactivity compared to their corresponding homodimers [57]. BMP receptors (BMPRs) belong to the group of serine/threonine kinase transmembrane receptors and are subdivided into type I and II receptors [64][65]. There are three type I receptors, namely BMPR-IA (also known as ALK-3, activin
PDF
Album
Review
Published 13 May 2015
Graphical Abstract
  • derivatives of many amino acids often become annoyingly strenuous due to the necessity of employing protecting groups, on one or more of the amino acid functionalities, during the synthetic sequence. However, in the case of hydroxyamino acids such as hydroxyproline, serine, threonine, tyrosine and 3,4
  • ; organocatalysis; serine; threonine; tyrosine; Introduction Any adept researcher within the field of organic synthetic chemistry will be mindful of the outstanding importance of amino acids as inexpensive chiral starting materials in the synthesis of a nearly infinite variety of synthetic end products. This
  • the copper salt with hydrogen sulfide. This methodology has subsequently been employed in a more generic sense as a preparative method for synthesis of acrylic side-chain derivatives of amino acids such as lysine, ornithine, tyrosine and serine [6][7][8], having modified the original technique by
PDF
Album
Review
Published 08 Apr 2015

Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

  • Vicky Gheerardijn,
  • Jos Van den Begin and
  • Annemieke Madder

Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268

Graphical Abstract
  • functionalities on the nucleoside. As proof of principle and with the catalytic serine–histidine–aspartate catalytic triad of serine proteases in mind, we illustrate the preparation of three different nucleosides equipped with three functional amino acids containing hydroxy, imidazole, amine and carboxylate
  • assembly of the desired chain without DNA damage. In the current study, we have chosen to couple three amino acids, which contain functional groups commonly used in SELEX approaches to modify DNA or RNA, to 5-iodo-2’-deoxyuridine. We describe the direct and linker-less introduction of histidine, serine and
  • accomplished under standard conditions and the corresponding derivative 5 was isolated and purified without problems. As a second example we decided to employ serine as amino acid for introduction onto the nucleoside. In view of the earlier illustrated need for imidazole protection during introduction of
PDF
Album
Supp Info
Full Research Paper
Published 04 Nov 2014

Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

  • Michael Kurlemann and
  • Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253

Graphical Abstract
  • Supporting Information File 1). The di- and trivalent guest strands 8–14 (Figure 1C, D) were synthesized by solid phase peptide synthesis using a standard Fmoc-protocol (Figure 3). Therefore the serine derivatives 15 and 16 (Figure 1E) and a water-soluble linker molecule were used. The purity of the guest
  • strands is estimated to be >95% based on 1H NMR spectra (see Supporting Information File 1). The syntheses of the multivalent host and guest strands are described in detail in Supporting Information File 1. First of all, the selectivity of the complexation of the unprotected serine derivatives 17 and 18
  • towards α- and β-CD was investigated by ITC experiments. The structures of the host–guest complexes were elucidated by NMR spectroscopy. The 1-adamantane-functionalized serine 17 shows complexation of α- and β-CD, forming 1:1 complexes. In both cases the adamantane moiety binds into the CD cavity, which
PDF
Album
Supp Info
Full Research Paper
Published 20 Oct 2014

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

  • Thilo Focken and
  • Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

Graphical Abstract
  • -workers led to a reassignment of its structure and that of the parent molecules, such as polyoxin A (69) [24][25][26]. The synthesis of the E-isomer of polyoximic acid started from protected D-serine 70, which was converted into diazoketone 71 by reacting a mixed anhydride with diazomethane (Scheme 10
PDF
Album
Review
Published 13 Aug 2014

Carbohydrate PEGylation, an approach to improve pharmacological potency

  • M. Eugenia Giorgi,
  • Rosalía Agusti and
  • Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

Graphical Abstract
  • is transferred to the glycan by a sialyltransferase. The serine or threonine residues in the O-glycosylation sites serve as acceptors for GalNAc using a convenient GalNAc transferase. This unit can be galactosylated by a galactosyltransferase and both, the monosaccharide and the disaccharide, may be
PDF
Album
Review
Published 25 Jun 2014

Amino acid motifs in natural products: synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

  • Oliver Ries,
  • Martin Büschleb,
  • Markus Granitzka,
  • Dietmar Stalke and
  • Christian Ducho

Beilstein J. Org. Chem. 2014, 10, 1135–1142, doi:10.3762/bjoc.10.113

Graphical Abstract
  • -α-amino acids serine and threonine, (2S,3S)-3-hydroxyleucine can be found as a substructure of several bioactive natural products. This structural motif often serves as a 'three-way-junction', as for instance in azinothricin [1], citropeptin [2], kettapeptin [3], pipalamycin [4], dentigerumycin [5
  • protecting group pattern. The most promising strategy to achieve these goals appeared to be a variation of the ex-chiral pool synthesis developed by Zhu and co-workers [32]. They have utilized the stereocenter of D-serine in a diastereoselective Grignard addition to protected D-serinal as the key step of
  • [32], we have employed their 7-step synthesis of a stereoisomerically pure amino alcohol as the key intermediate. According to the previously reported protocol, D-serine (2) was transformed into protected derivative 3 (4 steps, 59% overall yield, Scheme 1). Alcohol 3 was then oxidized to a D-serinal
PDF
Album
Supp Info
Full Research Paper
Published 16 May 2014

Stereocontrolled synthesis of 5-azaspiro[2.3]hexane derivatives as conformationally “frozen” analogues of L-glutamic acid

  • Beatrice Bechi,
  • David Amantini,
  • Cristina Tintori,
  • Maurizio Botta and
  • Romano di Fabio

Beilstein J. Org. Chem. 2014, 10, 1114–1120, doi:10.3762/bjoc.10.110

Graphical Abstract
  • the identification of new potent and selective ligands of ionotropic and metabotropic glutamate receptors (GluRs). To this aim, bicycle compound Ib was designed and synthesised from D-serine as novel [2.3]-spiro analogue of L-Glu. This frozen amino acid derivative was designed to further limit the
  • from D-serine, their synthesis was accomplished in 10 steps in good overall yield. After an extensive investigation on the best synthetic approach, key intermediate 20 was successfully prepared by an efficient rhodium-catalyzed cyclopropanation of a terminal double bond of compound 18 with ethyl
PDF
Album
Supp Info
Full Research Paper
Published 14 May 2014

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

  • Michał Górny vel Górniak,
  • Anna Czernicka,
  • Piotr Młynarz,
  • Waldemar Balcerzak and
  • Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 741–745, doi:10.3762/bjoc.10.68

Graphical Abstract
  • acids and their short peptides are a class of well-established inhibitors of serine proteases [11][12]. Their mechanism of action involves phosphonylation of the active-site of these enzymes with simultaneous release of the appropriate phenol [13][14]. Therefore, the synthesis of such inhibitors
  • carrying fluorescent probes in their side chains or in the ester phosphonate moieties might find an application in constructing fluorescent probes for studying structural requirements of enzymes having serine in their active sites (proteinases and phosphatases) or to study their elevated level in various
PDF
Album
Supp Info
Full Research Paper
Published 28 Mar 2014

Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis

  • Frank Hahn,
  • Nadine Kandziora,
  • Steffen Friedrich and
  • Peter F. Leadlay

Beilstein J. Org. Chem. 2014, 10, 634–640, doi:10.3762/bjoc.10.55

Graphical Abstract
  • be conveniently obtained by loading coenzyme A (CoA) thioesters onto active site serine residues of recombinant ACPs by using 4'-phosphopantetheinyl transferases [12][14]. However, coenzyme A thioesters are synthetically hard to access, especially if the substrate structure is complex. Results and
PDF
Album
Supp Info
Full Research Paper
Published 11 Mar 2014

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

  • Gijs Koopmanschap,
  • Eelco Ruijter and
  • Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

Graphical Abstract
  • and triazines, whereas azepines form an important class of seven-membered cyclic peptidomimetics. Four membered ring constraints β-Lactams The smallest class of cyclic peptidomimetics is that of the β-lactams. β-lactams are effective antibiotics [30] but also show inhibitory activities against serine
PDF
Album
Review
Published 04 Mar 2014
Other Beilstein-Institut Open Science Activities