Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures

2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation in mixtures of creatinine, phenylalanine, amino acids and 4-oxo-2-nonenal was studied, to analyse the role of amino acids on the generation of this heterocyclic aromatic amine. When oxidised lipid was absent, cysteine, serine, aspartic acid, threonine, asparagine, tryptophan, tyrosine, proline, and methionine increased significantly (p < 0.05) the amount of PhIP formed in comparison to the control. When lipid was present, only the addition of methionine, glycine, and serine increased significantly (p < 0.05) the amount of PhIP produced, while histidine, cysteine, lysine, tryptophan, tyrosine, and alanine reduced significantly (p < 0.05) PhIP. These results may be a consequence of the different competitive reactions that occur. Thus, in the absence of lipids, thermal decomposition of the amino acids produced reactive carbonyls that converted phenylalanine into phenylacetaldehyde as a key step in the formation of PhIP. When oxidised lipid was present, amino acids competed with phenylalanine for the lipid, and amino acid degradation products were formed, among which alpha-keto acids seemed to play a role in these reactions. These results suggest that PhIP can be produced by several alternative reaction pathways from all major food components, including amino acids and lipids, in addition to carbohydrates.     

鲜切果蔬苯丙烷代谢的研究进展

新鲜果蔬经切割处理后,生理代谢发生紊乱,产品品质大大降低。同时,果蔬机体产生积极的应对反应,通过诱导苯丙烷代谢途径中防御酶活性的提高和多酚、黄酮、木质素等的积累,对机械胁迫起到防御作用。本文通过综述切割后果蔬苯丙烷代谢关键酶以及主要中间产物和最终产物的变化,讨论切割对果蔬苯丙烷代谢的促进作用。      

制备低苯丙氨酸特膳食品的研究进展

低苯丙氨酸特膳食品是苯丙酮尿症患者日常饮食所需的食品,但目前仍存在苯丙氨酸不达标、大多人工合成、安全性不足等问题,因此制备低苯丙氨酸特膳食品备受关注。本文就蛋白原料的筛选、蛋白中苯丙氨酸的游离、苯丙氨酸的吸附、特膳食品的开发等方面进行综述,重点围绕苯丙氨酸充分游离与高效脱除进行分析,同时指出目前该研究领域中存在的酶制剂特异性不足、吸附剂专一性不够等问题,并对未来的研究重点进行展望,以期为低苯丙氨酸特膳食品的制备研究及其产品研发提供参考。     

苯丙氨酸及苯丙酮酸对Lactobacillus sp. SK007合成苯乳酸的影响

从自然发酵泡菜中分离筛选到一株乳杆菌(Lactobacillus sp.)SK007,研究了Lactobacillus sp. SK007利用苯丙氨酸合成苯乳酸的过程,结果发现,在MRS培养基中最高可产生0.55 mmol/L苯乳酸,苯丙氨酸剩余94%,但检测不到中间产物苯丙酮酸,这表明苯丙氨酸的转氨反应是苯乳酸合成的限速步骤. 用苯丙酮酸代替苯丙氨酸作为底物可有效突破这一瓶颈,进一步优化了Lactobacillus sp. SK007利用苯丙酮酸合成苯乳酸的发酵条件. 当苯丙酮酸为18.3 mmol/L, 30℃静置培养24 h,苯乳酸产量可达10.25 mmol/L.     

The response of phenylalanine ammonia‐lyase,polyphenol oxidase and phenols to cold stress in the olive tree (Olea europaea L. cv. Picual)

BACKGROUND: In this study the activities of phenylalanine ammonia‐lyase (PAL) and polyphenol oxidase (PPO) and the concentrations of hydroxytyrosol, tyrosol and oleuropein in olive tree (Olea europaea L. cv. Picual) leaves were investigated before and after cold stress by freezing. The air temperature fell to below ?7 °C and, according to the specific field conditions, four categories of orchard were selected: not cold stressed (NS), lightly cold stressed (LS), moderately cold stressed (MS) and heavily cold stressed (HS). RESULTS: In LS and MS samples the PAL specific activity at saturated substrate concentration rose 4.8‐ and 1.9‐fold respectively compared with NS samples. In HS samples the PAL activity declined by 47% compared with NS samples. A low level of PAL protein was detected in all samples affected by cold stress. In LS, MS and HS samples the PPO specific activity at saturated substrate concentration was 1.9‐, 4.4‐ and 9.8‐fold higher respectively than in NS samples. K_m values also increased after cold stress. In MS and HS samples the concentration of oleuropein was 69 and 82% higher respectively than in NS samples, while the concentrations of hydroxytyrosol and tyrosol decreased. CONCLUSION: The response of PAL activity may be part of a recovery process of the olive leaf against cold stress, while the response of PPO and oleuropein may be part of an antioxidant protection mechanism. Copyright © 2009 Society of Chemical Industry     

The first report on the atom transfer radical polymerization of an optically active acidic monomer based on L‐phenylalanine

For the first time, acidic monomer chiral N‐acryloyl‐L ‐phenylalanine was polymerized directly by atom transfer radical polymerization under mild conditions. Controlled polymerization was carried out in pure water, methanol/water mixture, or pure methanol using water‐soluble initiators, such as 2‐hydroxyethyl‐2′‐methyl‐2′‐bromopropionate and sodium‐4‐(bromomethyl)benzoate at room temperature. The corresponding optically active biocompatible amino acid‐based homopolymers were obtained in good yields with narrow molecular weight distributions. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Fabrication of capped gold nanoparticles by using various amino acids

The production of gold nanoparticles (GNPs) by amino acid is one of the most attractive and interesting subjects in nanobiotechnology. In this study, amino acids have been utilised as a reducing agent and also an agent for capping GNPs. The GNPs were prepared using a reduction solution containing gold cations with optimum concentration of gold salt (5?mM), and also functionalised by glutamic acid, phenylalanine and tryptophan with optimum concentration of amino acids (25?mM). The optimum condition of gold solution and amino acids were achieved by ultraviolet–visible spectroscopy. The size of nanoparticles was obtained 5–20, 10–20 and 20–30?nm, respectively, by transmission electron microscopy and dynamic light scattering techniques. The results obtained from experimental and quantum calculations confirm that amino acids have strong bond while they have anion binding. Moreover, the free carboxylic groups of capped GNPs are one of the suitable and capable beads for binding biological agents. As a result, the medical applications of amino acids and proteins can be used as a practical method due to the strong interaction of peripheral amine groups with nanoparticles.     

L-乳酸和α-苯丙氨酸聚酯酰胺共聚物的合成表征及降解

以直接熔融缩聚法成功制备了L-乳酸和α-苯丙氨酸聚酯酰胺共聚物.采用红外光谱、核磁共振、凝胶色谱、差示扫描量热仪和X射线衍射等对共聚物结构和性能进行了分析测试,重点考察了投料比对产物组成、分子量及其热性能和结晶性能的影响,并对共聚物的降解性能进行了初步试验.随着α-苯丙氨酸含量增加,相应共聚物的分子量明显下降,结晶性下...     

Synthesis and characterization of novel triblock copolymers comprising poly(tetrahydrofuran) as a central block and poly(γ-benzyl L-glutamate)s as outer blocks

Background Bioactive and biodegradable polyurethanes (BDPUs) have drawn much attention in recent years. As part of the research program to search for novel prepolymers for BDPUs, a study was carried out on the synthesis and characterization of triblock copolymers comprising poly(tetrahydrofuran) as a central block and poly(γ-benzyl L-glutamate)s as outer blocks. Results A new macroinitiator terminated with phenylalanine was first prepared from the condensation of a distal hydroxy poly(tetrahydrofuran) with N-tert-butoxycarbonyl L-phenylalanine in the presence of dicyclohexylcarbodiimide, followed by removing the protecting group. Then, it was employed to initiate the ring-opening polymerization of γ-benzyl L-glutamate N-carboxyanhydride in varying feeding ratios to give rise to the targeted triblock copolymers. Conclusions The length of the outer poly(γ-benzyl L-glutamate) blocks was well tailored by varying the monomers to macroinitiator feeding ratio. All the triblock copolymers exhibited a nearly symmetrical and unimodal molecular weight distribution while only one distinct glass transition temperature was evidenced from −10°C to 25°C.     

Synthesis of new optically active poly(amide‐imide)s containing EPICLON and L‐phenylalanine in the main chain by microwave irradiation and classical heating

EPICLON [3a,4,5,7a‐Tetrahydro‐7‐methyl‐5‐(tetrahydro‐2,5‐dioxo‐3‐furanyl)‐1,3‐isobenzofurandione] or [5‐(2,5‐dioxotetrahydrofurfuryl)‐3‐methyl‐3‐cyclohexyl‐1,2‐dicarboxylic acid anhydride] ( 1 ) was reacted with L ‐phenylalanine ( 2 ) in acetic acid, and the resulting amic acid was refluxed under a Dean‐Stark system with benzene, which produced diacid ( 3 ) in high yield. Compound ( 3 ) was converted to the diacid chloride ( 4 ) by reaction with oxalyl chloride in dry carbon tetrachloride. The polycondensation reaction of this diacid chloride ( 4 ) with several aromatic diamines such as 4,4′‐sulfonyldianiline ( 5a ), 4,4′‐diaminodiphenylmethane ( 5b ), 4,4′‐diaminodiphenylether ( 5c ), 1,4‐phenylenediamine ( 5d ), 1,3‐phenylenediamine ( 5e ), 2,4‐diaminotoluene ( 5f ), and 1,5‐diaminonaphthalene ( 5g ) was developed by using a domestic microwave oven in the presence of a small amount of a polar organic medium such as N‐methylpyrrolidone ( NMP ). The polymerization reactions were also performed under two different classical heating methods: low temperature solution polycondensation in the presence of trimethylsilyl chloride, and high temperature polymerization. A series of optically active poly(amide‐imide)s with moderate yield and inherent viscosity of 0.14–0.22 dL/g were obtained. All of the above polymers were fully characterized by IR, elemental analyses, and specific rotation. Some structural characterization and physical properties of this optically active poly(amide‐imide)s are reported. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 91: 3281–3291, 2004