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Article ; Online: Electrochemical Azidooxygenation of Alkenes Mediated by a TEMPO-N

Siu, Juno C / Sauer, Gregory S / Saha, Ambarneil / Macey, Reed L / Fu, Niankai / Chauviré, Timothée / Lancaster, Kyle M / Lin, Song

Journal of the American Chemical Society

2018 Volume 140, Issue 39, Page(s) 12511–12520

Abstract: ... N difunctionalized compounds from simple alkenes. Detailed mechanistic studies revealed a distinct ... complex with azide, TEMPO-N ...

Abstract	We report a mild and efficient electrochemical protocol to access a variety of vicinally C-O and C-N difunctionalized compounds from simple alkenes. Detailed mechanistic studies revealed a distinct reaction pathway from those previously reported for TEMPO-mediated reactions. In this mechanism, electrochemically generated oxoammonium ion facilitates the formation of azidyl radical via a charge-transfer complex with azide, TEMPO-N
MeSH term(s)	Azides/chemistry ; Chemistry Techniques, Synthetic ; Cyclic N-Oxides/chemistry ; Electrochemical Techniques ; Kinetics ; Spectrophotometry, Ultraviolet
Chemical Substances	Azides ; Cyclic N-Oxides ; TEMPO (VQN7359ICQ)
Language	English
Publishing date	2018-09-12
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.8b06744
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Article ; Online: Seaweed biogeochemistry: Global assessment of C:N and C:P ratios and implications for ocean afforestation.

Sheppard, Emily J / Hurd, Catriona L / Britton, Damon D / Reed, Daniel C / Bach, Lennart T

Journal of phycology

2023 Volume 59, Issue 5, Page(s) 879–892

Abstract: Algal carbon-to-nitrogen (C:N) and carbon-to-phosphorus (C:P) ratios are fundamental ... Australia (51 species, 10 locations) to update the global ratios of seaweed carbon-to-nitrogen (C:N) and ... carbon-to-phosphorus (C:P). The updated global mean molar ratio for seaweed C:N is 20 (ranging from 6 ...

Abstract	Algal carbon-to-nitrogen (C:N) and carbon-to-phosphorus (C:P) ratios are fundamental for understanding many oceanic biogeochemical processes, such as nutrient flux and climate regulation. We synthesized literature data (444 species, >400 locations) and collected original samples from Tasmania, Australia (51 species, 10 locations) to update the global ratios of seaweed carbon-to-nitrogen (C:N) and carbon-to-phosphorus (C:P). The updated global mean molar ratio for seaweed C:N is 20 (ranging from 6 to 123) and for C:P is 801 (ranging from 76 to 4102). The C:N and C:P ratios were significantly influenced by seawater inorganic nutrient concentrations and seasonality. Additionally, C:N ratios varied by phyla. Brown seaweeds (Ochrophyta, Phaeophyceae) had the highest mean C:N of 27.5 (range: 7.6-122.5), followed by green seaweeds (Chlorophyta) of 17.8 (6.2-54.3) and red seaweeds (Rhodophyta) of 14.8 (5.6-77.6). We used the updated C:N and C:P values to compare seaweed tissue stoichiometry with the most recently reported values for plankton community stoichiometry. Our results show that seaweeds have on average 2.8 and 4.0 times higher C:N and C:P than phytoplankton, indicating seaweeds can assimilate more carbon in their biomass for a given amount of nutrient resource. The stoichiometric comparison presented herein is central to the discourse on ocean afforestation (the deliberate replacement of phytoplankton with seaweeds to enhance the ocean biological carbon sink) by contributing to the understanding of the impact of nutrient reallocation from phytoplankton to seaweeds under large-scale seaweed cultivation.
Language	English
Publishing date	2023-08-19
Publishing country	United States
Document type	Journal Article
ZDB-ID	281226-5
ISSN	1529-8817 ; 0022-3646
ISSN (online)	1529-8817
ISSN	0022-3646
DOI	10.1111/jpy.13381
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Article ; Online: Exploring reactivity and product formation in N(

Nieman, Reed / Spezia, Riccardo / Jayee, Bhumika / Minton, Timothy K / Hase, William L / Guo, Hua

The Journal of chemical physics

2020 Volume 153, Issue 18, Page(s) 184702

Abstract: ... simulations of atomic-nitrogen [N( ...

Abstract	Atomic nitrogen is formed in the high-temperature shock layer of hypersonic vehicles and contributes to the ablation of their thermal protection systems (TPSs). To gain atomic-level understanding of the ablation of carbon-based TPS, collisions of hyperthermal atomic nitrogen on representative carbon surfaces have recently be investigated using molecular beams. In this work, we report direct dynamics simulations of atomic-nitrogen [N(
Language	English
Publishing date	2020-11-13
Publishing country	United States
Document type	Journal Article
ZDB-ID	3113-6
ISSN	1089-7690 ; 0021-9606
ISSN (online)	1089-7690
ISSN	0021-9606
DOI	10.1063/5.0028253
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Article ; Online: Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides.

Reed, Hayley / Paul, Tyler R / Chain, William J

The Journal of organic chemistry

2018 Volume 83, Issue 18, Page(s) 11359–11368

Abstract: The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access ... bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation ... of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N ...

Abstract	The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N- O bond via treatment with thionyl bromide or thionyl chloride at low temperature.
MeSH term(s)	Aniline Compounds/chemical synthesis ; Aniline Compounds/chemistry ; Chemistry Techniques, Synthetic ; Halogenation ; Oxides/chemistry
Chemical Substances	Aniline Compounds ; Oxides
Language	English
Publishing date	2018-08-09
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.8b01590
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Article ; Online: Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols.

Reed-Berendt, Benjamin G / Morrill, Louis C

The Journal of organic chemistry

2019 Volume 84, Issue 6, Page(s) 3715–3724

Abstract: An efficient manganese-catalyzed N-alkylation of sulfonamides has been developed. This borrowing ... alkyl sulfonamides undergoes mono- N-alkylation in excellent isolated yields (32 examples, 85% average yield). ...

Abstract	An efficient manganese-catalyzed N-alkylation of sulfonamides has been developed. This borrowing hydrogen approach employs a well-defined and bench-stable Mn(I) PNP pincer precatalyst, allowing benzylic and simple primary aliphatic alcohols to be employed as alkylating agents. A diverse range of aryl and alkyl sulfonamides undergoes mono- N-alkylation in excellent isolated yields (32 examples, 85% average yield).
Language	English
Publishing date	2019-02-21
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.9b00203
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Article ; Online: An N-terminal fusion allele to study melanin concentrating hormone receptor 1.

Jasso, Kalene R / Kamba, Tisianna K / Zimmerman, Arthur D / Bansal, Ruchi / Engle, Staci E / Everett, Thomas / Wu, Chang-Hung / Kulaga, Heather / Reed, Randal R / Berbari, Nicolas F / McIntyre, Jeremy C

Genesis (New York, N.Y. : 2000)

2021 Volume 59, Issue 7-8, Page(s) e23438

Abstract: ... mCherry into the N-terminus of Mchr1. Analysis of the fusion protein ( ...

Abstract	Cilia on neurons play critical roles in both the development and function of the central nervous system (CNS). While it remains challenging to elucidate the precise roles for neuronal cilia, it is clear that a subset of G-protein-coupled receptors (GPCRs) preferentially localize to the cilia membrane. Further, ciliary GPCR signaling has been implicated in regulating a variety of behaviors. Melanin concentrating hormone receptor 1 (MCHR1), is a GPCR expressed centrally in rodents known to be enriched in cilia. Here we have used MCHR1 as a model ciliary GPCR to develop a strategy to fluorescently tag receptors expressed from the endogenous locus in vivo. Using CRISPR/Cas9, we inserted the coding sequence of the fluorescent protein mCherry into the N-terminus of Mchr1. Analysis of the fusion protein (
MeSH term(s)	Alleles ; Animals ; Cilia/metabolism ; Homozygote ; Melanins/metabolism ; Mice ; Mice, Inbred C57BL ; Neurons/metabolism ; Neurons/physiology ; Receptors, Somatostatin/genetics ; Receptors, Somatostatin/metabolism ; Synapses/metabolism ; Synapses/physiology ; Synaptic Potentials
Chemical Substances	Mchr1 protein, mouse ; Melanins ; Receptors, Somatostatin
Language	English
Publishing date	2021-06-14
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	2004544-X
ISSN	1526-968X ; 1526-954X
ISSN (online)	1526-968X
ISSN	1526-954X
DOI	10.1002/dvg.23438
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Article ; Online: An N-Ethyl-N-Nitrosourea (ENU)-Induced Tyr265Stop Mutation of the DNA Polymerase Accessory Subunit Gamma 2 (Polg2) Is Associated With Renal Calcification in Mice.

Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research

2018 Volume 34, Issue 3, Page(s) 497–507

Abstract: ... abdominal X-rays to identify renal opacities in N-ethyl-N-nitrosourea (ENU)-mutagenized mice ...

Abstract	Renal calcification (RCALC) resulting in nephrolithiasis and nephrocalcinosis, which affects ∼10% of adults by 70 years of age, involves environmental and genetic etiologies. Thus, nephrolithiasis and nephrocalcinosis occurs as an inherited disorder in ∼65% of patients, and may be associated with endocrine and metabolic disorders including: primary hyperparathyroidism, hypercalciuria, renal tubular acidosis, cystinuria, and hyperoxaluria. Investigations of families with nephrolithiasis and nephrocalcinosis have identified some causative genes, but further progress is limited as large families are unavailable for genetic studies. We therefore embarked on establishing mouse models for hereditary nephrolithiasis and nephrocalcinosis by performing abdominal X-rays to identify renal opacities in N-ethyl-N-nitrosourea (ENU)-mutagenized mice. This identified a mouse with RCALC inherited as an autosomal dominant trait, designated RCALC type 2 (RCALC2). Genomewide mapping located the Rcalc2 locus to a ∼16-Mbp region on chromosome 11D-E2 and whole-exome sequence analysis identified a heterozygous mutation in the DNA polymerase gamma-2, accessory subunit (Polg2) resulting in a nonsense mutation, Tyr265Stop (Y265X), which co-segregated with RCALC2. Kidneys of mutant mice (Polg2
MeSH term(s)	Animals ; Calcinosis/genetics ; Calcinosis/metabolism ; Calcinosis/pathology ; Codon, Terminator ; DNA Polymerase gamma/genetics ; DNA Polymerase gamma/metabolism ; Ethylnitrosourea/toxicity ; Kidney/metabolism ; Kidney/pathology ; Kidney Diseases/genetics ; Kidney Diseases/metabolism ; Kidney Diseases/pathology ; Mice ; Mice, Mutant Strains
Chemical Substances	Codon, Terminator ; DNA Polymerase gamma (EC 2.7.7.7) ; Polg protein, mouse (EC 2.7.7.7) ; Ethylnitrosourea (P8M1T4190R)
Language	English
Publishing date	2018-12-14
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	632783-7
ISSN	1523-4681 ; 0884-0431
ISSN (online)	1523-4681
ISSN	0884-0431
DOI	10.1002/jbmr.3624
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Article ; Online: Half-life extension of peptidic APJ agonists by N-terminal lipid conjugation.

Reed, Anthony B / Lanman, Brian A / Holder, Jerry Ryan / Yang, Bryant H / Ma, Ji / Humphreys, Sara C / Wang, Zhican / Chan, Joyce C Y / Miranda, Les P / Swaminath, Gayathri / Allen, John G

Bioorganic & medicinal chemistry letters

2020 Volume 30, Issue 21, Page(s) 127499

Abstract: Agonism of the endothelial receptor APJ (putative receptor protein related to ... ...

Abstract	Agonism of the endothelial receptor APJ (putative receptor protein related to AT
MeSH term(s)	Animals ; Apelin Receptors/agonists ; Apelin Receptors/metabolism ; Dose-Response Relationship, Drug ; Injections, Intravenous ; Lipids/administration & dosage ; Lipids/chemistry ; Lipids/pharmacology ; Molecular Structure ; Myocardial Infarction/drug therapy ; Myocardial Infarction/metabolism ; Peptides/administration & dosage ; Peptides/chemistry ; Peptides/pharmacology ; Rats ; Structure-Activity Relationship
Chemical Substances	Apelin Receptors ; Aplnr protein, rat ; Lipids ; Peptides
Language	English
Publishing date	2020-08-26
Publishing country	England
Document type	Journal Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2020.127499
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Article ; Online: Seaweed biogeochemistry: Global assessment of C:N and C:P ratios and implications for ocean afforestation

Sheppard, Emily J. / Hurd, Catriona L. / Britton, Damon D. / Reed, Daniel C. / Bach, Lennart T.

Journal of Phycology. 2023 Oct., v. 59, no. 5 p.879-892

2023

Abstract: Algal carbon‐to‐nitrogen (C:N) and carbon‐to‐phosphorus (C:P) ratios are fundamental ... Australia (51 species, 10 locations) to update the global ratios of seaweed carbon‐to‐nitrogen (C:N) and ... carbon‐to‐phosphorus (C:P). The updated global mean molar ratio for seaweed C:N is 20 (ranging from 6 ...

Abstract	Algal carbon‐to‐nitrogen (C:N) and carbon‐to‐phosphorus (C:P) ratios are fundamental for understanding many oceanic biogeochemical processes, such as nutrient flux and climate regulation. We synthesized literature data (444 species, >400 locations) and collected original samples from Tasmania, Australia (51 species, 10 locations) to update the global ratios of seaweed carbon‐to‐nitrogen (C:N) and carbon‐to‐phosphorus (C:P). The updated global mean molar ratio for seaweed C:N is 20 (ranging from 6 to 123) and for C:P is 801 (ranging from 76 to 4102). The C:N and C:P ratios were significantly influenced by seawater inorganic nutrient concentrations and seasonality. Additionally, C:N ratios varied by phyla. Brown seaweeds (Ochrophyta, Phaeophyceae) had the highest mean C:N of 27.5 (range: 7.6–122.5), followed by green seaweeds (Chlorophyta) of 17.8 (6.2–54.3) and red seaweeds (Rhodophyta) of 14.8 (5.6–77.6). We used the updated C:N and C:P values to compare seaweed tissue stoichiometry with the most recently reported values for plankton community stoichiometry. Our results show that seaweeds have on average 2.8 and 4.0 times higher C:N and C:P than phytoplankton, indicating seaweeds can assimilate more carbon in their biomass for a given amount of nutrient resource. The stoichiometric comparison presented herein is central to the discourse on ocean afforestation (the deliberate replacement of phytoplankton with seaweeds to enhance the ocean biological carbon sink) by contributing to the understanding of the impact of nutrient reallocation from phytoplankton to seaweeds under large‐scale seaweed cultivation.
Keywords	Chlorophyta ; Phaeophyceae ; Rhodophyta ; afforestation ; algology ; biomass ; carbon ; carbon sinks ; climate ; macroalgae ; phytoplankton ; seawater ; seaweed culture ; stoichiometry ; Tasmania
Language	English
Dates of publication	2023-10
Size	p. 879-892.
Publishing place	John Wiley & Sons, Ltd
Document type	Article ; Online
Note	JOURNAL ARTICLE
ZDB-ID	281226-5
ISSN	1529-8817 ; 0022-3646
ISSN (online)	1529-8817
ISSN	0022-3646
DOI	10.1111/jpy.13381
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Automated Preparation of MS-Sensitive Fluorescently Labeled N-Glycans with a Commercial Pipetting Robot.

Reed, Corey E / Fournier, Jennifer / Vamvoukas, Nikolaos / Koza, Stephan M

SLAS technology

2018 Volume 23, Issue 6, Page(s) 550–559

Abstract: N-Glycan analysis is routinely performed for biotherapeutic protein characterization. A recently ... introduced N-glycan analysis kit using RapiFluor-MS (RFMS) labeling provides time savings over reductive ... two heating and cooling steps during protein denaturation and de-N-glycosylation. However, the current ...

Abstract	N-Glycan analysis is routinely performed for biotherapeutic protein characterization. A recently introduced N-glycan analysis kit using RapiFluor-MS (RFMS) labeling provides time savings over reductive amination labeling methods while also providing enhanced fluorescence (FLR) and mass spectrometry (MS) responses. This article demonstrates the semiautomation of this kit using an Andrew Alliance pipetting robot that promises further gains in productivity. This robotic platform uses standard manual pipettors and an optically guided arm to facilitate the automation of manual procedures. The manual RFMS protocol includes two heating and cooling steps during protein denaturation and de-N-glycosylation. However, the current Andrew Alliance automated platform cannot move reaction tubes to and from different heating blocks. As a result, samples prepared using the automated procedure remain in a computer-controlled Peltier effect heating block, requiring reoptimization of denaturation and de-N-glycosylation temperatures. Using hydrophilic interaction liquid chromatography to monitor the RFMS-labeled glycan profiles, the authors demonstrated the reproducibility of the automated protocol with percent relative standard deviations (RSDs) of 9%-19% for the total area and 0.8%-20% for the relative areas of major and minor glycoforms. Overall, the automated platform presented here proves to be a convenient and reliable solution for N-glycan preparation and analysis.
MeSH term(s)	Automation, Laboratory/methods ; Fluorescent Dyes/metabolism ; Mass Spectrometry/instrumentation ; Mass Spectrometry/methods ; Polysaccharides/analysis ; Proteins/chemistry ; Reproducibility of Results ; Robotics/instrumentation ; Staining and Labeling/instrumentation ; Staining and Labeling/methods
Chemical Substances	Fluorescent Dyes ; Polysaccharides ; Proteins
Language	English
Publishing date	2018-04-04
Publishing country	United States
Document type	Journal Article
ZDB-ID	2900310-6
ISSN	2472-6311 ; 2472-6303
ISSN (online)	2472-6311
ISSN	2472-6303
DOI	10.1177/2472630318762384
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