Synthesis of an amino acid analogue to incorporate p-aminobenzyl-EDTA in peptides.
A convenient and straightforward synthesis of an amino acid analog, [p-(N-alpha-Fmoc-L-aspartic acid-beta-amido)benzyl]-EDTA tetra-tert-butyl ester, compatible with Fmoc solid phase peptide synthesis strategy is described. This reagent was used to incorporate p-aminobenzyl-EDTA at an internal sequence position in an HIV-1 Tat protein fragment. After cleavage from the resin and standard deprotection, the peptide was purified by high-performance liquid chromatography and characterized by mass spectrometry. Through this methodology, flexible linkers of different lengths and containing various structures can be placed between the alpha-carbon backbone of peptides and metal chelates. These peptides will provide a new class of affinity cleaving reagents that can be directed against protein and nucleic acid targets.
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Department of Pharmacology, Robert Wood Johnson Medical School, University of Medicine and Dentistry of New Jersey, Piscataway 08854, USA.
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D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002614:Chelating Agents / Q000138:chemical synthesis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004492:Edetic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015696:Gene Products, tat / Q000138:chemical synthesis / Q000737:chemistry / Q000235:genetics; D015497:HIV-1 / Q000737:chemistry / Q000235:genetics; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D054322:tat Gene Products, Human Immunodeficiency Virus
C106666:(4-(N-alpha-fluorenylmethoxycarbonyl-aspartic acid beta-amido)benzyl)EDTA tetra tert-butyl ester; D000596:Amino Acids; D002614:Chelating Agents; D015696:Gene Products, tat; D007202:Indicators and Reagents; D010455:Peptides; D054322:tat Gene Products, Human Immunodeficiency Virus; D001224:Aspartic Acid; C057690:aminobenzyl-EDTA; D004492:Edetic Acid