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Study on Synthesis of Dipeptide and Glucose Glycopeptide by Phthalyl Anhydride

Author: HuangYueFang
Tutor: YangChunLong
School: Nanjing Agricultural College
Course: Pesticides
Keywords: Dipeptide Glucose peptide Synthesis Crystal structure Biological Activity
CLC: TQ450.1
Type: Master's thesis
Year: 2008
Downloads: 91
Quote: 0
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Abstract


Glycopeptides of carbohydrates covalently linked to form peptides, glycopeptides retain the basic core of the glycoprotein carbohydrate - peptide linker regions, but not as large molecular weight glycoprotein complex structure, is an important model for studies glycoprotein. Some, such as glycopeptides Ningnanmycin, Cytosinpeptidemycin with broad-spectrum anti-viral, anti-fungal and plant pathogenic nematicidal activity. The subject of the use of phthalic anhydride synthesis of a series of peptide compounds glucose and bactericidal activity conducted a preliminary experiment, hoping to develop a new type of environmentally friendly and efficient fungicide. This phthalic anhydride used as the amino-protecting agent 6 kinds of synthesized phthaloyl amino acids. Focuses on the phthaloyl glycine synthesis conditions, the optimal reaction conditions for the reaction temperature of 140 ℃, reaction time 30 min, n (Gly): n (phthalic anhydride) = 1:1.2, yield 95.6 %. Simultaneous determination of phthaloyl glycine monohydrate crystal structure, the crystal belongs to monoclinic, P 21 / n space group, a = 7.6380 (15) nm, b = 13.803 (3) nm, c = 10.009 (2) nm, β = 106.67 (3) °, Z = 4, Dc = 1.466 g · cm -3 , μ = 0.120 mm -1 , F (000 ) = 464. The final factor R = 0.0606, wR = 0.1647. Crystal structure analysis shows the intermolecular hydrogen bonding molecules to form along the [010] direction, zigzag long chain, and through π-π stacking to form a stable three-dimensional structure. The remaining five kinds of phthaloyl amino acid is also used for IR and MS identification of the structure. Using isobutyl chloroformate was synthesized as carboxyl activator phthaloyl glycylglycine seven kinds of amino protected dipeptide. Using hydrazine hydrate in a weak alkaline solution and stirred at room temperature removal of the amino protecting group, to obtain glycyl glycine dipeptide, etc. 3. Structure of the product through the infrared spectrum of the initial identification. 2 - glucosamine hydrochloride and phthalimido compound peptide solution in DMF, DCC synthesized under the effect of 7 kinds of direct condensation of the protected amino-peptide compounds glucose. Product was subjected to column chromatographic separation, purification, and for the melting point, IR and mass measurement. Meanwhile peptide compounds of glucose were measured indoors early bactericidal activity was found on glucose test peptide compounds that vegetable plant pathogens Botrytis cinerea (Botrytis cinera), Rhizoctonia (Rhizoctoniacerealis), Fusarium graminearum (Gibberella zeae ) and Fusarium moniliforme (Fussrium moniliforme) have some bactericidal activity. Ⅳ b bactericidal activity which is higher.

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