当前位置： SCI文献检索 > Nature Protocols期刊下所有文献 > Synthesis of enantiomerically enriched (R)-5-tert-butylazepan-2-one using a hydroxyalkyl azide mediated ring-expansion reaction.

Synthesis of enantiomerically enriched (R)-5-tert-butylazepan-2-one using a hydroxyalkyl azide mediated ring-expansion reaction.

Abstract：

:A procedure for the conversion of a symmetrical ketone to an enantiomerically pure lactam is described. The technique described here involves a ring-expansion reaction of a 4-substituted cyclohexanone accomplished with a chiral 1,3-azidopropanol derivative. The procedure entails first a one-step preparation of (R)-1-phenyl-3-azidopropanol from a commercially available halide precursor, which is then reacted with the ketone using BF(3) x OEt(2) as a Lewis acid promoter. The resulting lactam is subsequently converted into a chiral lactam of high enantiopurity via the two-stage removal of the chiral nitrogen substituent. The present protocol carries out the diastereoselective ring-expansion reaction with higher selectivity than competing processes and is generally useful for the preparation of 5-substituted caprolactams.

journal_name

Nat Protoc

journal_title

Nature protocols

authors

Ribelin TP,Aubé J

doi

10.1038/nprot.2007.518

subject

Has Abstract

pub_date

2008-01-01 00:00:00

pages

137-43

issue

1

eissn

1754-2189

issn

1750-2799

pii

nprot.2007.518

journal_volume

3

pub_type

杂志文章

相关文献

Nature Protocols文献大全
  • A strategy for co-translational folding studies of ribosome-bound nascent chain complexes using NMR spectroscopy.

    abstract：:During biosynthesis on the ribosome, an elongating nascent polypeptide chain can begin to fold, in a process that is central to all living systems. Detailed structural studies of co-translational protein folding are now beginning to emerge; such studies were previously limited, at least in part, by the inherently dyna...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2016.101

    authors： Cassaignau AM,Launay HM,Karyadi ME,Wang X,Waudby CA,Deckert A,Robertson AL,Christodoulou J,Cabrita LD

    更新日期：2016-08-01 00:00:00

  • Monitoring lymphocyte proliferation in vitro and in vivo with the intracellular fluorescent dye carboxyfluorescein diacetate succinimidyl ester.

    abstract：:This protocol outlines the carboxyfluorescein diacetate succinimidyl ester (CFSE) method for following the proliferation of human lymphocytes in vitro and mouse lymphocytes both in vitro and in vivo. The method relies on the ability of CFSE to covalently label long-lived intracellular molecules with the highly fluores...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2007.296

    authors： Quah BJ,Warren HS,Parish CR

    更新日期：2007-01-01 00:00:00

  • Spheroid-based human endothelial cell microvessel formation in vivo.

    abstract：:The study of angiogenic endothelial cells (ECs) has in recent years greatly stimulated multiple fields of vascular biology research. A number of cellular models and numerous complex developmental, manipulatory and tumor animal models have been developed to study angiogenesis in vitro and in vivo. To connect the versat...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2009.96

    authors： Laib AM,Bartol A,Alajati A,Korff T,Weber H,Augustin HG

    更新日期：2009-01-01 00:00:00

  • A whole-tissue RNA-seq toolkit for organism-wide studies of gene expression with PME-seq.

    abstract：:The immune system operates at the scale of the whole organism in mammals. We currently lack experimental approaches to systematically track and study organism-wide molecular processes in mice. Here we describe an integrated toolkit for measuring gene expression in whole tissues, 3-prime mRNA extension sequencing, that...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/s41596-019-0291-y

    authors： Pandey S,Takahama M,Gruenbaum A,Zewde M,Cheronis K,Chevrier N

    更新日期：2020-04-01 00:00:00

  • Collecting, rearing, spawning and inducing regeneration of the starlet sea anemone, Nematostella vectensis.

    abstract：:Over the past 20 years, the starlet sea anemone, Nematostella vectensis, a small estuarine animal, has emerged as a powerful model system for field and laboratory studies of development, evolution, genomics, molecular biology and toxicology. Here we describe how to collect Nematostella, culture it through its entire s...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2013.044

    authors： Stefanik DJ,Friedman LE,Finnerty JR

    更新日期：2013-05-01 00:00:00

  • High-throughput ballistic injection nanorheology to measure cell mechanics.

    abstract：:High-throughput ballistic injection nanorheology is a method for the quantitative study of cell mechanics. Cell mechanics are measured by ballistic injection of submicron particles into the cytoplasm of living cells and tracking the spontaneous displacement of the particles at high spatial resolution. The trajectories...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2011.436

    authors： Wu PH,Hale CM,Chen WC,Lee JS,Tseng Y,Wirtz D

    更新日期：2012-01-05 00:00:00

  • Robust phosphoproteome enrichment using monodisperse microsphere-based immobilized titanium (IV) ion affinity chromatography.

    abstract：:Mass spectrometry (MS)-based proteomics has become the preferred tool for the analysis of protein phosphorylation. To be successful at such an endeavor, there is a requirement for an efficient enrichment of phosphopeptides. This is necessary because of the substoichiometric nature of phosphorylation at a given site an...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2013.010

    authors： Zhou H,Ye M,Dong J,Corradini E,Cristobal A,Heck AJ,Zou H,Mohammed S

    更新日期：2013-03-01 00:00:00

  • Fabrication of nanopores with ultrashort single-walled carbon nanotubes inserted in a lipid bilayer.

    abstract：:We describe a protocol for the insertion of ultrashort single-walled carbon nanotubes (SWCNTs) to form nanopores in a Montal-Mueller lipid bilayer. The SWCNTs are designed to bind to a specific analyte of interest; binding will result in the reduction of current in single-channel recording experiments. The first stage...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2015.112

    authors： Liu L,Xie J,Li T,Wu HC

    更新日期：2015-11-01 00:00:00

  • Polyethylene glycol-based bidentate ligands to enhance quantum dot and gold nanoparticle stability in biological media.

    abstract：:We describe a simple and versatile scheme to prepare a series of poly(ethylene glycol)-based bidentate ligands that permit strong interactions with colloidal semiconductor nanocrystals (quantum dots, QDs) and gold nanoparticles (AuNPs) alike and promote their dispersion in aqueous solutions. These ligands are synthesi...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2008.243

    authors： Mei BC,Susumu K,Medintz IL,Mattoussi H

    更新日期：2009-01-01 00:00:00

  • Measuring bone blood supply in mice using fluorescent microspheres.

    abstract：:Fluorescent microspheres are commonly used to assess bone blood supply in large animals, but the technique is not widely used in smaller mammals, as traditional methods such as reference blood sampling, ventilation and catheterization are not easily applied. This protocol describes a viable alternative for measuring b...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2009.190

    authors： Serrat MA

    更新日期：2009-01-01 00:00:00

  • Fluorescence resonance energy transfer microscopy as demonstrated by measuring the activation of the serine/threonine kinase Akt.

    abstract：:This protocol describes procedures for performing fluorescence resonance energy transfer (FRET) microscopy analysis by three different methods: acceptor photobleaching, sensitized emission and spectral imaging. We also discuss anisotropy and fluorescence lifetime imaging microscopy-based FRET techniques. By using the ...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2012.147

    authors： Broussard JA,Rappaz B,Webb DJ,Brown CM

    更新日期：2013-02-01 00:00:00

  • Investigation of higher-order RNA G-quadruplex structures in vitro and in living cells by 19F NMR spectroscopy.

    abstract：:Growing evidence indicates that RNA G-quadruplexes have important roles in various processes such as transcription, translation, regulation of telomere length, and formation of telomeric heterochromatin. Investigation of RNA G-quadruplex structures associated with biological events is therefore essential to understand...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2017.156

    authors： Bao HL,Xu Y

    更新日期：2018-04-01 00:00:00

  • Standardization of complex biologically derived spectrochemical datasets.

    abstract：:Spectroscopic techniques such as Fourier-transform infrared (FTIR) spectroscopy are used to study interactions of light with biological materials. This interaction forms the basis of many analytical assays used in disease screening/diagnosis, microbiological studies, and forensic/environmental investigations. Advantag...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/s41596-019-0150-x

    authors： Morais CLM,Paraskevaidi M,Cui L,Fullwood NJ,Isabelle M,Lima KMG,Martin-Hirsch PL,Sreedhar H,Trevisan J,Walsh MJ,Zhang D,Zhu YG,Martin FL

    更新日期：2019-05-01 00:00:00

  • A protocol for isolation and culture of mesenchymal stem cells from mouse compact bone.

    abstract：:Unlike humans, mouse bone marrow-derived mesenchymal stem cells (MSCs) cannot be easily harvested by adherence to plastic owing to the contamination of cultures by hematopoietic cells. The design of the protocol described here is based on the phenomenon that compact bones abound in MSCs and hematopoietic cells exist i...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2009.238

    authors： Zhu H,Guo ZK,Jiang XX,Li H,Wang XY,Yao HY,Zhang Y,Mao N

    更新日期：2010-03-01 00:00:00

  • Cloning of ground-state intestinal stem cells from endoscopic biopsy samples.

    abstract：:'Adult' or 'somatic' stem cells harbor an intrinsic ability to regenerate tissues. Heterogeneity of such stem cells along the gastrointestinal tract yields the known segmental specificity of this organ and may contribute to the pathology of certain enteric conditions. Here we detail technology for the generation of 'l...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/s41596-020-0298-4

    authors： Duleba M,Yamamoto Y,Neupane R,Rao W,Xie J,Qi Y,Liew AA,Niroula S,Zhang Y,Mahalingam R,Wang S,Goller K,Ajani JA,Vincent M,Ho KY,Hou JK,Hyams JS,Sylvester FA,Crum CP,McKeon F,Xian W

    更新日期：2020-05-01 00:00:00

  • Directed differentiation of human pluripotent cells to neural crest stem cells.

    abstract：:Multipotent neural crest stem cells (NCSCs) have the potential to generate a wide range of cell types including melanocytes; peripheral neurons; and smooth muscle, bone, cartilage and fat cells. This protocol describes in detail how to perform a highly efficient, lineage-specific differentiation of human pluripotent c...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2012.156

    authors： Menendez L,Kulik MJ,Page AT,Park SS,Lauderdale JD,Cunningham ML,Dalton S

    更新日期：2013-01-01 00:00:00

  • RNase H-dependent PCR-enabled T-cell receptor sequencing for highly specific and efficient targeted sequencing of T-cell receptor mRNA for single-cell and repertoire analysis.

    abstract：:RNase H-dependent PCR-enabled T-cell receptor sequencing (rhTCRseq) can be used to determine paired alpha/beta T-cell receptor (TCR) clonotypes in single cells or perform alpha and beta TCR repertoire analysis in bulk RNA samples. With the enhanced specificity of RNase H-dependent PCR (rhPCR), it achieves TCR-specific...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/s41596-019-0195-x

    authors： Li S,Sun J,Allesøe R,Datta K,Bao Y,Oliveira G,Forman J,Jin R,Olsen LR,Keskin DB,Shukla SA,Wu CJ,Livak KJ

    更新日期：2019-08-01 00:00:00

  • Radiolabeling of HYNIC-annexin V with technetium-99m for in vivo imaging of apoptosis.

    abstract：:Apoptosis is a critical factor in AIDS and other viral illnesses, cerebral and myocardial ischemia, autoimmune and neurodegenerative states, organ and bone marrow transplant rejection, and tumor response to chemotherapy and radiation. Improved methods to identify sites of apoptosis are increasing our understanding of ...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2006.17

    authors： Blankenberg FG,Vanderheyden JL,Strauss HW,Tait JF

    更新日期：2006-01-01 00:00:00

  • Ex vivo perfusion of mid-to-late-gestation mouse placenta for maternal-fetal interaction studies during pregnancy.

    abstract：:Ex vivo perfusion systems offer a reliable, reproducible method for studying acute physiological responses of an organ to various environmental manipulations. Unlike in vitro culture systems, the cellular organization, compartmentalization and three-dimensional structure of ex vivo-perfused organs are maintained. Thes...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2012.144

    authors： Goeden N,Bonnin A

    更新日期：2013-01-01 00:00:00

  • Enhanced delivery of cell-penetrating peptide-peptide nucleic acid conjugates by endosomal disruption.

    abstract：:Improvement of cellular uptake and cellular localization is still one of the main obstacles to the development of antisense-antigene therapeutics, including peptide nucleic acid (PNA). Cell-penetrating peptides (CPPs) such as Tat peptide and polyarginine have been widely used to improve the cellular uptake of PNA and ...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2006.92

    authors： Shiraishi T,Nielsen PE

    更新日期：2006-01-01 00:00:00

  • Determining the polysaccharide composition of plant cell walls.

    abstract：:The plant cell wall is a chemically complex structure composed mostly of polysaccharides. Detailed analyses of these cell wall polysaccharides are essential for our understanding of plant development and for our use of plant biomass (largely wall material) in the food, agriculture, fabric, timber, biofuel and biocompo...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2012.081

    authors： Pettolino FA,Walsh C,Fincher GB,Bacic A

    更新日期：2012-09-01 00:00:00

  • τ-SGA: synthetic genetic array analysis for systematically screening and quantifying trigenic interactions in yeast.

    abstract：:Systematic complex genetic interaction studies have provided insight into high-order functional redundancies and genetic network wiring of the cell. Here, we describe a method for screening and quantifying trigenic interactions from ordered arrays of yeast strains grown on agar plates as individual colonies. The proto...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/s41596-020-00456-3

    authors： Kuzmin E,Rahman M,VanderSluis B,Costanzo M,Myers CL,Andrews BJ,Boone C

    更新日期：2021-01-18 00:00:00

  • Proteome-wide identification of SUMO modification sites by mass spectrometry.

    abstract：:The protein called 'small ubiquitin-like modifier' (SUMO) is post-translationally linked to target proteins at the ɛ-amino group of lysine residues. This 'SUMOylation' alters the behavior of the target protein, a change that is utilized to regulate diverse cellular processes. Understanding the target-specific conseque...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2015.095

    authors： Tammsalu T,Matic I,Jaffray EG,Ibrahim AF,Tatham MH,Hay RT

    更新日期：2015-09-01 00:00:00

  • Synthesis and use of an amphiphilic dendrimer for siRNA delivery into primary immune cells.

    abstract：:Using siRNAs to genetically manipulate immune cells is important to both basic immunological studies and therapeutic applications. However, siRNA delivery is challenging because primary immune cells are often sensitive to the delivery materials and generate immune responses. We have recently developed an amphiphilic d...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/s41596-020-00418-9

    authors： Chen J,Ellert-Miklaszewska A,Garofalo S,Dey AK,Tang J,Jiang Y,Clément F,Marche PN,Liu X,Kaminska B,Santoni A,Limatola C,Rossi JJ,Zhou J,Peng L

    更新日期：2021-01-01 00:00:00

  • 5' end-centered expression profiling using cap-analysis gene expression and next-generation sequencing.

    abstract：:Cap-analysis gene expression (CAGE) provides accurate high-throughput measurement of RNA expression. CAGE allows mapping of all the initiation sites of both capped coding and noncoding RNAs. In addition, transcriptional start sites within promoters are characterized at single-nucleotide resolution. The latter allows t...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2012.005

    authors： Takahashi H,Lassmann T,Murata M,Carninci P

    更新日期：2012-02-23 00:00:00

  • A surgical orthotopic organoid transplantation approach in mice to visualize and study colorectal cancer progression.

    abstract：:Most currently available colorectal cancer (CRC) mouse models are not suitable for studying progression toward the metastatic stage. Recently, establishment of tumor organoid lines, either from murine CRC models or patients, and the possibility of engineering them with genome-editing technologies, have provided a larg...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2017.137

    authors： Fumagalli A,Suijkerbuijk SJE,Begthel H,Beerling E,Oost KC,Snippert HJ,van Rheenen J,Drost J

    更新日期：2018-02-01 00:00:00

  • Preparation of aptamer-linked gold nanoparticle purple aggregates for colorimetric sensing of analytes.

    abstract：:Aptamers are single-stranded DNA or RNA molecules that can bind target molecules with high affinity and specificity. The conformation of an aptamer usually changes upon binding to its target analyte, and this property has been used in a wide variety of sensing applications, including detection based on fluorescence in...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2006.38

    authors： Liu J,Lu Y

    更新日期：2006-01-01 00:00:00

  • Cytokinesis-block micronucleus cytome assay.

    abstract：:The cytokinesis-block micronucleus cytome assay is a comprehensive system for measuring DNA damage, cytostasis and cytotoxicity. DNA damage events are scored specifically in once-divided binucleated (BN) cells and include (a) micronuclei (MNi), a biomarker of chromosome breakage and/or whole chromosome loss, (b) nucle...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2007.77

    authors： Fenech M

    更新日期：2007-01-01 00:00:00

  • Multiparametric characterization of rare HIV-infected cells using an RNA-flow FISH technique.

    abstract：:Efforts to cure HIV are hampered by limited characterization of the cells supporting HIV replication in vivo and inadequate methods for quantifying the latent viral reservoir in individuals receiving antiretroviral therapy (ART). We describe a protocol for flow cytometric identification of viral reservoirs, based on c...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2017.079

    authors： Baxter AE,Niessl J,Fromentin R,Richard J,Porichis F,Massanella M,Brassard N,Alsahafi N,Routy JP,Finzi A,Chomont N,Kaufmann DE

    更新日期：2017-10-01 00:00:00

  • Expander: from expression microarrays to networks and functions.

    abstract：:A major challenge in the analysis of gene expression microarray data is to extract meaningful biological knowledge out of the huge volume of raw data. Expander (EXPression ANalyzer and DisplayER) is an integrated software platform for the analysis of gene expression data, which is freely available for academic use. It...

    journal_title：Nature protocols

    pub_type： 杂志文章

    doi：10.1038/nprot.2009.230

    authors： Ulitsky I,Maron-Katz A,Shavit S,Sagir D,Linhart C,Elkon R,Tanay A,Sharan R,Shiloh Y,Shamir R

    更新日期：2010-02-01 00:00:00