双语化学辞典Chem Lexicon
类别 · 生物化学 · 糖类 Biochemistry · Carbohydrates

碳水化合物Carbohydrate

拼音Pinyin tàn shuǐ huà hé wù 别名Also 糖类;糖;saccharide; sugar

定义Definition

碳水化合物(糖类)是多羟基醛、多羟基酮以及能水解生成它们的化合物的总称,按能否水解及水解产物分为单糖、寡糖(如二糖)和多糖。许多糖的通式为 Cₘ(H₂O)ₙ,“碳水化合物”之名由此而来,但这一通式并不严格。

Carbohydrates (saccharides) are polyhydroxy aldehydes and ketones and the compounds that hydrolyse to them. By hydrolysis they are classed as monosaccharides, oligosaccharides such as disaccharides, and polysaccharides. Many have the general formula Cₘ(H₂O)ₙ, which gave rise to the name 'hydrate of carbon', though the formula does not hold strictly.

分类与结构Classes and structure

单糖按羰基位置分为醛糖和酮糖,按碳数分为丙糖、戊糖、己糖等,如葡萄糖(己醛糖)、果糖(己酮糖)、核糖(戊醛糖)。五碳以上的单糖在水溶液中主要以五元(呋喃糖)或六元(吡喃糖)环状半缩醛形式存在,并产生 α、β 端基异构体。通式例外如脱氧核糖 C₅H₁₀O₄ 不符合 Cₘ(H₂O)ₙ,而甲醛 CH₂O、乙酸 C₂H₄O₂ 符合通式却不是糖。

Monosaccharides are aldoses or ketoses according to the carbonyl position and trioses, pentoses, hexoses and so on by carbon count: glucose is an aldohexose, fructose a ketohexose and ribose an aldopentose. Those with five or more carbons exist in water mostly as five-membered (furanose) or six-membered (pyranose) cyclic hemiacetals with α and β anomers. Exceptions to the formula abound: deoxyribose, C₅H₁₀O₄, does not fit Cₘ(H₂O)ₙ, while formaldehyde (CH₂O) and acetic acid (C₂H₄O₂) fit it but are not sugars.

研究史History

19 世纪初人们从元素分析发现糖类中氢氧比为 2:1,以为是“碳的水合物”。1884–1891 年埃米尔·费歇尔用苯肼成脎反应鉴别糖类,并通过逻辑推理确定了葡萄糖等 16 种己醛糖的立体构型,获 1902 年诺贝尔化学奖。1920 年代哈沃斯确立了糖的环状结构并提出哈沃斯投影式。

In the early nineteenth century elemental analysis showed sugars contain hydrogen and oxygen in a 2:1 ratio, so they were thought to be hydrates of carbon. Between 1884 and 1891 Emil Fischer identified sugars by forming osazones with phenylhydrazine and reasoned out the configurations of glucose and the other aldohexoses, receiving the 1902 Nobel Prize in Chemistry. In the 1920s Haworth established the ring structures of sugars and introduced the Haworth projection.

生物功能Biological roles

糖类是生物体最主要的能源(每克约 17 kJ),也是结构物质(纤维素、甲壳素)、遗传物质的组成成分(核糖、脱氧核糖),并以糖蛋白、糖脂形式参与细胞识别、免疫和血型决定。中国居民膳食指南建议碳水化合物提供每日总能量的 50–65%。

Carbohydrates are the main energy source of living things (about 17 kJ per gram), structural materials (cellulose, chitin), components of genetic material (ribose, deoxyribose), and, as glycoproteins and glycolipids, take part in cell recognition, immunity and blood-group determination. Chinese dietary guidelines recommend that carbohydrates supply 50–65% of daily energy.

反应Reactions

Cₘ(H2O)ₙ + m O2 ⟶ m CO2 + n H2O

体内经糖酵解、三羧酸循环和氧化磷酸化完全氧化。

Fully oxidised in the body by glycolysis, the citric acid cycle and oxidative phosphorylation.

C12H22O11 浓 H2SO4⟶ 12 C + 11 H2OC12H22O11 conc. H2SO4⟶ 12 C + 11 H2O

浓硫酸使蔗糖炭化

Concentrated sulfuric acid chars sucrose

葡萄糖 + 3 PhNHNH2 ⟶ 葡萄糖脎 + PhNH2 + NH3 + 2 H2OGlucose + 3 PhNHNH2 ⟶ Glucose + PhNH2 + NH3 + 2 H2O

成脎反应

Osazone formation

年表Timeline

  • 1812

    基希霍夫发现淀粉可水解为葡萄糖

    Kirchhoff finds starch hydrolyses to glucose

  • 1884

    费歇尔用苯肼研究糖类

    Fischer begins using phenylhydrazine on sugars

  • 1891

    费歇尔确定葡萄糖构型

    Fischer determines the configuration of glucose

  • 1926

    哈沃斯提出糖的环状结构

    Haworth proposes ring structures for sugars