151 uv vis detector

Optical rotations were determined using a Jasco DIP-370 automatic polarimeter (Jasco, Tokyo, Japan). The NMR spectra were recorded using a BRUKER AVANCE III 600 (¹H, 600 MHz; ¹³C, 150 MHz) (Bruker Biospin GmbH, Karlsruhe, Germany), with tetramethylsilane (TMS) as an internal standard. Heteronuclear multiple quantum correlation (HMQC), heteronuclear multiple bond correlation (HMBC), rotating frame nuclear overhauser effect spectroscopy (ROESY), and ¹H–¹H correlation spectroscopy (COSY) spectra were recorded using a pulsed field gradient. The HR-ESI-MS spectra were obtained by using an Aglient 1200 LC-MSD Trap spectrometer (Agilent, Santa Clara, CA, USA). Preparative HPLC was performed using a GILSON 321 pump, 151 UV–VIS detector (Gilson, VILLIERS-LE-BEL, France), and RStech HECTOR-M C₁₈ column (5-micron, 250 × 21.2 mm) (RS Tech Crop, Chungju, South Korea). Column chromatography was performed using a silica gel (Kieselgel 60, 70–230, and 230–400 mesh, Merck, Darmstadt, Germany), YMC C-18 resins, and thin layer chromatography (TLC) was performed using pre-coated silica-gel 60 F₂₅₄ and RP-18 F_254S plates (both 0.25 mm, Merck, Darmstadt, Germany). The spots were detected under UV light and using 10% H₂SO₄. The adjacent torsion angles were measured by Chemdraw 3D (version 17.1).

Lactose-oligonucleotide conjugates were synthesized by conjugating allyl lactose with thiol-modified oligonucleotides via photochemical reaction using a photoinitiator^{55 (link)}. Single-stranded oligonucleotides (Supplementary Table 1) pretreated with 1,4-dithiothreitol (100 nmol, 1 equiv.), 1-O-allyl-D-lactose (100 nmol, 1 equiv.), and photoinitiator (10 nmol, DMPA) were mixed in 1 mL of deionized water. The mixture was stirred under UV light (365 nm) using a UVP Blak-Ray^® XX-15 L UV bench lamp (15 W; Analytik Jena, Upland, CA, USA) for 2 h. After the reaction, the mixture was analyzed by normal-phase high-performance liquid chromatography (HPLC; Gilson, Middleton, WI, USA) using an LC-321 and OD-300 column (4.6 mm × 250 mm; PerkinElmer, Waltham, MA, USA). The sample was eluted using a linear gradient of acetonitrile (25–100% (v/v)) in 0.1 M triethylammonium acetate (pH 7.0) and detected at 260 nm with a diode array detector (UV/Vis-151 detector; Gilson). Data were acquired using the TRILUTION^® LC software v 2 .1.

Liquid chromatography (LC) system included a UV/Vis-151 detector (Gilson), an autosampler (Gilson-234), and a LC-321/322/350 pump (Gilson, France). Detection and quantification were performed using a Synergi Hydro-RP C18 column (250 × 4.6 mm, 4 μm, 80 Å; Phenomenex, USA). The flow rate was maintained at 0.8 ml/min for lactate. Isocratic mobile phases included 0.1% phosphoric acid in water for lactate. After extraction, the samples were transferred to a sample tube with acetonitrile containing thiamine (internal standard) and mixed thoroughly. The samples were centrifuged for 5 min at 1503×g. The supernatants were analyzed by performing HPLC (LC-321/322/350 pump) at 210 nm for lactate.

Optical rotations were measured on a JASCO P-2000 polarimeter using a 1-cm cell. UV and electronic circular dichroism (ECD) spectra were recorded on a Chirascan CD spectrometer (Applied Photophysics, Surrey, UK). 1D and 2D NMR spectra were obtained with Bruker AVANCE III HD 850 spectrometers (Bruker, Billerica, MA, USA) at the National Center for Interuniversity Research Facilities at Seoul National University (NCIRF). UHPLC-Q/TOF-MS analyses were performed on a Waters Acquity UPLC system (Waters Co., Milford, MA, USA) coupled with a Waters Xevo G2 QTOF mass spectrometer (Waters MS Technologies, Manchester, UK) that was equipped with an electrospray interface (ESI). The absolute configurations of the amino acids in compounds 1 and 2 were determined using an Agilent 6120 quadruple MSD consisting of a 1260 Infinity pump, a 1260 Infinity autosampler, a 1260 Infinity DAD (Agilent Technologies, Santa Clara, CA, USA), and an Agilent Zorbax SB-C₃ column (150 × 4.6 mm, 5 μm) at 50 °C. Semi-preparative HPLC separations were performed with a system consisting of a Gilson 321 Pump and a UV/Vis-151 detector (Gilson Inc., Middleton, WI, USA). Extra-pure grade solvents for extraction, fractionation, and isolation were purchased from Dae Jung Pure Chemical Engineering Co. Ltd., Siheung, Korea. Deuterated DMSO for NMR analyses was purchased from Merck (Darmstadt, Germany).

¹H, ¹³C, and 2D (COSY, HSQC, HMBC) nuclear magnetic resonance (NMR) spectra were measured in methanol-d₄ using Bruker Avance 600 MHz spectrometers (Bruker, Billerica, MA, USA) at the National Instrumentation Center for Environmental Management (NICEM) of Seoul National University. Liquid chromatography/mass spectrometry (LC/MS) data were obtained with an Agilent Technologies 6130 quadrupole mass spectrometer (Agilent Technologies, Santa Clara, CA, USA) coupled with an Agilent Technologies 1200 series high-performance liquid chromatography (HPLC) instrument. High-resolution fast atom bombardment (HR-FAB) mass spectra were recorded on a Jeol JMS-700 high-resolution mass spectrometer (Jeol, Tokyo, Japan) at the National Center for Inter-University Research Facilities (NCIRF) of Seoul National University. HPLC was performed using a Gilson 321 HPLC pump with a Gilson UV/VIS-151 detector (Gilson, Middleton, WI, USA). All solvents used were of spectroscopic grade or were distilled prior to use.