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4 protocols using cyclopropylamine

1

Glyoxal Reactions with Amines

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Glyoxal (40% wt in H2O), benzylamine (99%), cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine, and allylamine were purchased from Sigma Aldrich. 4-Bromobenzylamine was purchased from Oakwood Chemical. Formic acid (LiChropur) and 4-Methoxybenzylamine were purchased from EMD Millipore, and acetonitrile (HPLC LC–MS grade) was purchased from VWR chemical. Glyoxal stock solutions (10 mM) were made containing 0% formic acid (FA), 0.1% FA, 1% FA, 5% FA, and 10% FA. Solutions for each amine (8 total) were 20 mM. 500 µL of Glyoxal with FA and 500 µL of amine variants were combined to create the reaction mixture, resulting in reaction solutions containing 10 mM amine, 5 mM Glyoxal, and FA (0%, 0.05%, 0.5%, 2.5%, 5%).
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2

Synthesis and Characterization of Sulfanilamide Derivatives

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All of the reagents and
chemicals were of analytical grade and purchased from commercial suppliers.
Sulfapyridine (NENTECH, U.K., 99%), sulfaguanidine (Tokyo Chemical
Industry, Japan, 98%), cyanuric chloride (Acros Organics, China, 99%),
aniline (GCC, U.K., 99.5%), benzylamine (LobaChemi, India, 99%), cyclopropylamine
(Sigma-Aldrich, 98%), cyclohexyl amine (Sigma-Aldrich, 99%), diethylamine
(GCC, U.K., 98%), m-toluidine (Sigma-Aldrich, 99%),
3,4-dimethylaniline (GCC, U.K., 98%), 4-chloroaniline (Sigma-Aldrich,
98%), 4-bromoaniline (Sigma-Aldrich, 90%), 4-fluoroaniline (Sigma-Aldrich,
99%), 4-nitroaniline (Janssen, Belgium, 98%), morpholine (Tokyo Chemical
Industry, Japan, 99%), acetone (Carlo Erba, France, 99%), ethanol
(Carlo Erba, France, 98%), dimethylformamide (DMF) (Carlo Erba, France,
99.9%), n-hexane (Carlo Erba, France, 95%), sodium
bicarbonate (NaHCO3) (GCC, U.K., 99.5%), sodium hydroxide
(NaOH) (GCC, U.K., 99.5%), triethylamine (TEA) (TEDIA, 99%), chloroform
(Carlo Erba, France, 99.9%) and dimethyl sulfoxide (DMSO) (Carlo Erba,
France, 99%).
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3

Silicon (111) Surface Functionalization

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In this experiment, P-type silicon (111) (0.001–0.005 Ω cm) was ordered from Semiconductor Wafer, Inc. (Hsinchu, Taiwan). Cyclopropylamine (98%), 3-Butyn-1-ol (97%), Mesitylene (98%), Hydrogen peroxide (30%), Hydrofluoric acid (ACS reagent, 48%) as well as sulfuric acid (99.99%) were acquired from Sigma-Aldrich (St Louis, MO, USA), except where noted, and used with no further purification.
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4

Comprehensive Analytical Reagents Protocol

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2,2‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS), 2,6‐dimethoxyphenol (2,6‐DMP), 1‐hydroxybenzotriazole (HBT), tyramine, dopamine, phenylethylamine, putrescine, N‐(3‐dimethyl aminopropyl)‐N’‐ethylcarbodiimide (EDC), 1,10‐phenanthroline, 2,2′‐bipyridyl, clorgyline, cyclopropylamine, deprenyl, pargyline HCl, rasagiline, semicarbazide, NaCl, NaF and molecular weight standard proteins were obtained from Sigma‐Aldrich (Madrid, Spain). 2,2,6,6‐tetramethylpiperidine 1‐oxyl free radical (TEMPO) was from TCI (Tokyo, Japan). Nickel‐chelating nitrilotriacetic acid (Ni+2‐NTA) agarose was from Qiagen (Hilden, Germany). All other chemicals and reagents were of analytical grade.
Restriction enzymes were obtained from New England Biolabs (Beverly, MA, USA), T4 DNA ligase was from Roche Diagnostics (Barcelona, Spain), and DNA polymerase was from Invitrogen (La Jolla, CA, USA).
The UltraClean® PCR Clean‐Up kit (Metabion) and the NZyMiniprep kit (Nzytech, Lisbon, Portugal) were used. DNA synthetic oligonucleotides were from Eurofins MWG Operon (Ebersberg, Germany).
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