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L-葡萄糖和D-葡萄糖單他糖兩大物質(zhì)特點(diǎn)
來源:http://la-lin.cn 日期:2019-06-21 發(fā)布人:admin
(一)物理性質(zhì)
(1) Physical properties
單糖都是無色晶體,味甜,有吸濕性。極易溶于水,難溶于乙醇,不溶于乙醚。單糖有旋光性,其溶液有變旋現(xiàn)象。
Monosaccharides are colorless crystals, sweet and hygroscopic. It is very soluble in water, insoluble in ethanol and insoluble in ether. Monosaccharides have optical rotation, and their solution has the phenomenon of rotation.
(二)化學(xué)性質(zhì)
(2) Chemical properties
單糖主要以環(huán)狀構(gòu)造方式存在,但在溶液中可與開鏈構(gòu)造反響。因而 ,單糖的化學(xué)反響有的以環(huán)式構(gòu)造停止,有的以開鏈構(gòu)造停止。
Monosaccharides mainly exist in the form of ring structure, but they can react with open-chain structure in solution. Therefore, some chemical reactions of monosaccharides stop with ring structure and others stop with open chain structure.
1.差向異構(gòu)化
1. Episomerization
葡萄糖用稀堿液處置時,會局部轉(zhuǎn)變?yōu)楦事短呛凸牵蔀閺?fù)雜的混合物。這咱變化是通老祖宗醇式中間體來完成的。
When the glucose is treated with dilute alkali solution, it will locally transform into mannose and fructose, and become a complex mixture. This change was accomplished by the alcoholic intermediates of Tonglao ancestors.
D-果糖、D-甘露糖和D-葡萄糖的C-3、C-4,C-5和C-6的構(gòu)造完整相同,只要C-1和C-2的構(gòu)造不同,但是它們的C-1,C-2的構(gòu)造互變成烯醇型時,其構(gòu)造完整相同的。因而,不單是D-葡萄糖,而D-果糖或D-甘露糖在稀堿催化下,都能互變?yōu)槿叩幕旌衔铩?/div>
The structures of C-3, C-4, C-5 and C-6 of D-fructose, D-mannose and D-glucose are identical, as long as the structures of C-1 and C-2 are different, but their C-1 and C-2 structures are identical when they become enol-like. Therefore, not only D-glucose, but also D-fructose or D-mannose can be mutually transformed into a mixture of the three under the catalysis of dilute alkali.
在含有多個手性碳原子的具有旋光性的異構(gòu)體之間,凡只要一個手性碳原子的構(gòu)型不同時,互稱為差向異構(gòu)體。D-葡萄糖和D-甘露糖就是C-2差向異構(gòu)體。因而,用稀堿處置D-葡萄糖得到D-葡萄糖、D-果糖三種物質(zhì)的均衡混合物的反響叫做差向異構(gòu)化。
Among the optically active isomers containing more than one chiral carbon atom, if only one chiral carbon atom has different configurations, they are called epimers. D-glucose and D-mannose are C-2 epimers. Therefore, the reaction of the equilibrium mixture of D-glucose and D-fructose obtained by treating D-glucose with dilute alkali is called epimerization.
2.氧化作用
2. Oxidation
單糖無論是醛糖或酮糖都可與弱的氧化劑葉倫試劑、費(fèi)林試劑和本尼迪特試劑作用,生成金屬或金屬的低價氧化物。上述三種試劑都是堿性的弱氧化劑。單糖在堿性溶液中加熱,生成復(fù)雜的混合物。
Monosaccharides, whether aldose or ketose, can react with weak oxidants such as Yellen reagent, Ferrin reagent and Benedict reagent to form low-valent oxides of metals or metals. The three reagents mentioned above are alkaline weak oxidants. Monosaccharides are heated in alkaline solutions to form complex mixtures.
單糖易被堿性弱氧化劑氧化闡明它們具有復(fù)原性,所以把它們叫做復(fù)原糖。
Monosaccharides are readily oxidized by alkaline weak oxidants to clarify their resilience, so they are called resilient sugars.
單糖在酸性條件下氧化時,由于氧化劑的強(qiáng)弱不同,單糖的氧化產(chǎn)物也不同。例如,葡萄糖被溴水氧化時,生成葡萄糖酸;而用強(qiáng)氧化劑硝酸氧化時,則生成葡萄糖二酸。
When monosaccharides are oxidized under acidic conditions, the oxidation products of monosaccharides are different because of the different oxidants. For example, when glucose is oxidized by bromine water, it produces gluconic acid, while when oxidized by nitric acid, it produces gluconic acid.
溴水氧化才能較弱,它把醛糖的醛基氧化 為羧基。當(dāng)醛糖中參加溴水,稍加熱后,溴水的棕色即可褪去,而酮糖則不被氧化,因而可用溴水來區(qū)別醛糖和酮糖。
無水葡萄糖
Bromine water oxidizes the aldehyde group of aldose to carboxyl group. When bromine water is added to aldose, the brown color of bromine water can be faded after a little heating, while ketose is not oxidized, so bromine water can be used to distinguish aldose from ketose.
3.成苷作用
3. Glycosidation
單糖環(huán)狀半縮醛構(gòu)造中的半縮醛羥基與另一分子醇或羥基作用時,脫去一分子水而生成縮醛。糖的這種縮醛稱為糖苷。例如α-和β-D-吡喃葡萄糖的混合物,在氯化氫催化下同甲醇反響,脫去一分子水,生成α-和β-D-甲基吡喃葡萄糖苷的混合物。
When the hydroxyl group of hemiacetal in the structure of monosaccharide cyclic hemiacetal reacts with another molecule alcohol or hydroxyl group, one molecule of water is removed to form acetal. This acetal of sugar is called glycoside. For example, a mixture of alpha-and beta-D-glucopyranose reacts with methanol catalyzed by hydrogen chloride, removes a molecule of water, and produces a mixture of alpha-and beta-D-methyl-glucopyranoside.
α-和β-D-吡喃葡萄混合液 β-D-甲基吡喃葡萄糖苷  α-D-甲基吡喃葡萄糖苷,苷由糖和非糖局部組成。非糖局部稱為糖苷配基或苷元。糖和糖苷配基脫水后經(jīng)過過“氧橋”銜接,這種鍵稱為苷鍵。由于單糖的環(huán)式構(gòu)造有α-和β-兩種構(gòu)型,所以可生成α-和β-兩種沒構(gòu)型的苷。自然苷多為β-構(gòu)型。苷的稱號是按其組成成分而命名的,并指出苷鍵和糖的構(gòu)型。自然苷常按其來源而用俗名。
The mixture of alpha-and beta-D-glucopyranoside is beta-D-methyl-glucopyranoside alpha-D-methyl-glucopyranoside, which is locally composed of sugar and non-sugar. Non-sugar is locally called glycoside ligand or aglycone. Sugar and glycoside ligands are dehydrated and then bonded by "oxygen bridge", which is called glycoside bond. Because the cyclic structure of monosaccharides has two configurations of alpha and beta, two kinds of non-configurable glycosides, alpha and beta, can be formed. Natural glycosides are mostly beta-configurations. Glycosides are named after their constituents, and the structures of glycoside bonds and sugars are pointed out. Natural glycosides are commonly used as common names according to their origin.
糖苷構(gòu)造中已沒有半縮醛羥基,在溶液中不能再轉(zhuǎn)變成開鏈的醛式構(gòu)造,所以糖工苷無復(fù)原性,也沒有變旋現(xiàn)象。糖苷在中性或堿性環(huán)境中較穩(wěn)定,但在酸性溶液中或在酶的作用下,則水解生成糖和非糖局部。
Glycosides have no semiacetal hydroxyl group and can no longer be converted into open-chain aldehyde structure in solution. Therefore, glycosides have no resilience and no rotation phenomenon. Glycosides are stable in neutral or alkaline environments, but in acidic solutions or under the action of enzymes, they hydrolyze to form sugars and non-sugars locally.
糖苷是中草藥的有效成分之一,多為無色、無臭、有苦澀味的固體,但黃酮苷和蒽醌苷為黃色。
Glycosides are one of the effective components of Chinese herbal medicine. Most of them are colorless, odorless, bitter and astringent solids, but flavonoid glycosides and anthraquinone glycosides are yellow.
苷中含有糖局部,所以在水中有一定的溶解性。苷類都有旋光性,自然苷多為左旋體。
Glycosides contain sugar locally, so they are soluble in water. Glycosides are optically active, and natural glycosides are mostly levotropic.
4.成酯作用
4. Esterification
單糖分子中含多個羥基,這些羥基能與酸作用生成酯。人體內(nèi)的葡萄糖在酶作用下生成葡萄糖磷酸酯,如1-磷酸吡喃葡萄糖和6-磷酸吡喃葡萄糖等。
Monosaccharide molecule contains many hydroxyl groups, which can react with acid to form esters. Glucose in human body produces glucose phosphate esters under the action of enzymes, such as 1-phosphate pyran glucose and 6-phosphate pyran glucose.
單糖的磷酸酯在生命過程中具有重要意義,它們是人體內(nèi)許多代謝的中間產(chǎn)物。
Phosphates of monosaccharides are important in the process of life. They are intermediate products of many metabolism in human body.
5.成脎反響
5. Chengsai Response
單糖分子與三分子苯肼作用,生成的產(chǎn)物叫做糖脎。例如葡萄糖與進(jìn)量苯肼作用,生成葡萄糖脎。
The monosaccharide molecule interacts with the three-molecule phenylhydrazine to produce a product called saccharose. For example, glucose reacts with phenylhydrazine to produce glucosamine.
無論是醛糖還是酮糖都能生成糖脎,成脎反響能夠看作是α-羥基醛或α-羥基酮的特有反響。
Both aldose and ketose can produce saccharose. The reaction of saccharose formation can be regarded as a specific reaction of alpha-hydroxyaldehyde or alpha-hydroxyacetone.
糖脎是難溶于水的黃色晶體。不同的脎具有特征的結(jié)晶外形和一定的熔點(diǎn)。常應(yīng)用糖脎和這些性質(zhì)來鑒別不同的糖。
Saccharine is a yellow crystal that is insoluble in water. Different samarium has characteristic crystalline shape and certain melting point. Sarcandra and these properties are often used to identify different sugars.
成脎反響只在單糖分子的C-1和C-2上發(fā)作,不觸及其它碳原子,因而除了C-1和C-2以外碳原子構(gòu)型相同的糖,都能夠生成相同的糖脎。例如:D-葡萄糖和D-果糖都 生成相同的脎。
Sarcandrium reactions occur only on C-1 and C-2 of monosaccharide molecules and do not touch other carbon atoms. Therefore, sugar with the same carbon atom configuration except C-1 and C-2 can produce the same saccharide. For example, D-glucose and D-fructose both produce the same anthraquinone.
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