研究目的
To synthesize cyclo-PLAI using a combination of solid- and solution-phase methods as an alternative to the previously reported method, aiming for a faster and more efficient synthesis.
研究成果
Cyclo-PLAI was successfully synthesized with a faster cyclization time (1.5 hours) and good yield (70%) compared to previous methods, demonstrating the efficiency of the combined solid- and solution-phase approach. The spectral data confirmed the structure, and the method offers a more straightforward synthesis pathway.
研究不足
The cyclization conditions required optimization to avoid dimer formation and achieve high yield; the method may not be generalizable to all cyclic peptides without further adjustments.
1：Experimental Design and Method Selection:
The synthesis employed a combination of solid-phase peptide synthesis (SPPS) for the linear precursor and solution-phase cyclization. The Fmoc/t-Bu strategy was used on 2-chlorotrityl resin, with HATU/HOAt as coupling reagents. Cyclization was optimized using HATU in DIPEA under specific temperature conditions.
2：Sample Selection and Data Sources:
The linear peptide precursor was synthesized from amino acids (Fmoc-L-Pro, Fmoc-L-Leu, Fmoc-L-Ala, Fmoc-L-Ile) and 2-chlorotrityl chloride resin. Spectral data were compared with previously reported data for cyclo-PLAI.
3：List of Experimental Equipment and Materials:
Instruments included analytical RP-HPLC (Waters), semi-preparative RP-MPLC (Buchi C-620 Sepacore), NMR spectrometer (Agilent 500 MHz), HR-TOF-MS (Waters), UV-Vis spectrophotometer (TECAN Infinite pro 200). Materials included 2-chlorotrityl chloride resin, amino acids, dichloromethane, DMF, TFA, piperidine, HATU, HOAt, DIPEA, acetonitrile.
4：0). Materials included 2-chlorotrityl chloride resin, amino acids, dichloromethane, DMF, TFA, piperidine, HATU, HOAt, DIPEA, acetonitrile. Experimental Procedures and Operational Workflow:
4. Experimental Procedures and Operational Workflow: The linear peptide was synthesized on resin through sequential Fmoc deprotection and coupling steps, monitored by chloranil test. Cleavage was done with 20% TFA in DCM. Purification used RP-MPLC. Cyclization was performed with HATU and DIPEA in DCM/DMF, stirred at 0°C for 1h and room temperature for 30min, followed by purification.
5：Data Analysis Methods:
Products were characterized using HR-TOF-MS, 1H-NMR, 13C-NMR, and analytical HPLC. Data were compared with literature values.
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NMR Spectrometer
Agilent NMR 500 MHz
Agilent
Recording 1H and 13C nuclear magnetic resonance spectra for structural characterization of compounds.
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2-chlorotrityl chloride resin
0.972 mmol/g
GL-Biochem Ltd.
Solid support for peptide synthesis, used to attach amino acids during solid-phase peptide synthesis.
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Analytical RP-HPLC
Waters 2998 Photodiode Array Detector, LiChrospher 100 RP-18 5 mm column
Waters
Analyzing the purity of peptides using reverse-phase high-performance liquid chromatography.
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Semi-preparative RP-MPLC
Buchi C-620 Sepacore, C18 column (12 g)
Buchi
Purifying peptides using medium-pressure liquid chromatography with a C18 column.
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HR-TOF-MS
Waters HR-TOF-MS Lockspray
Waters
Performing high-resolution time-of-flight mass spectrometry for accurate mass determination of compounds.
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UV-Vis Spectrophotometer
TECAN Infinite pro 200
TECAN
Measuring absorbance, used for monitoring resin loading in peptide synthesis.
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