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33544455890
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note
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1Abbreviations: AB, 3-(4-hydroxymethylphenoxy)propionic acid; AM, p{(R,S)-amino-2,4-dimethoxybenzyl}-phenoxyacetic acid; Boc, t-butoxycarbonyl; CD, circular dichroism; DBU, 1,8-diazabicyclo[5.4.0]-undec-7- ene; DCM, dichloromethane; DIEA, N,N′-diisopropylethylamine; DIPCDI, N,N′-diisopropylcarbodiimide; DMAP, 4-dimethylaminopiridine; DMF, N,N-dimethylformamide; EtOH, ethanol; ESI-MS, electrospray ionization mass spectrometry; Fmoc, 9-fluorenylmethoxycarbonyl; G2-4, second, third and fourth generation; AcOH, acetic acid; HOBt, 1-hydroxybenzotriazole; Imd, imidazolidine-2-carboxylic acid; MBHA resin, 4-methylbenzhydrylamine resin; MALDI-TOF, matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry; MeOH, methanol; NMP, 1-methyl-2-pyrrolidone; PyAOP, 7-aza-benzotriazol-1-yl-N-oxy-tris(pyrrolidino)-phosphonium hexafluorophosphate; RP-HPLC, reverse-phase high performance liquid chromatography; SEC, size exclusion chromatography; SPPS, solid-phase peptide synthesis; TFA, trifluoroacetic acid.
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2
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Although MS is considered a qualitative analytical method, in this case it is useful to determine small amount of deletion peptides, which are formed from the same residue, and therefore should have a response very similar to MS. Other techniques such as HPLC are not useful due to structural similarity of impurities.
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These signals came from the low percentage of Pro deletion in building block 1, and its intensity was amplified due the dendritic architecture itself.
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33544468300
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Several buffers were studied as mobile phases.
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33544463529
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This was taken as a reference to show that the presence of an additional residue of Gly does not disrupt the expected polyproline secondary structure.
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