不同结构类型糖类物质的荧光标记策略-西安齐岳生物
为阐明糖链结构与功能的关系，寻找高灵敏度和高分离度的微量分析方法对糖类物质的分
析至关重要． 近几年来，荧光标记方法作为糖类物质的色谱定量及辅助结构分析的选择，日益受到人们的广泛关注． 荧光标记法分为柱前标记和柱后标记两种，且灵敏度高、分离度好、有多种标记试剂可供选择． 本文根据不同糖类物质的结构特点，分别对中性糖和氨基糖以及含有唾液酸、糖醛酸、硫酸基的酸性糖的荧光标记方法及其应用进行了系统的综述，并对近年来报道的荧光标记试剂的特点和反应机理进行了比较和总结，以期为糖类物质微量分析方法的研究提供参考．
关键词中性糖; 氨基糖; 唾液酸; 糖醛酸; 荧光标记
1 the fluorescence labeling of neutral sugars
as the most popular method for neutral sugars，the labeling reaction which targets the lone electronpair of amino groups of reducing sugars is effective for the labeling to the carbon of carbonyl groups ( fig. 1) ．the common fluorescence labels are 2-aminopyridine，aminobenzene，aminonaphthalene sulfonic acid isomers and hydrazines．
2 the fluorescence labeling of amino sugars
the amino sugars have been extensively present in plants and animals． the amino groups or acetyl amino groups in sugars provide the opportunity for coupling reactions to form derivatives．
a novel sensitive fluorescent label of 9-fluorenylmethoxy chloroformate ( fmoc-cl) can readily
react with amino groups in sugars． fmoc sugar derivatives have a unique configuration ( i． e． ， β-form) at the reducing end，and have no isomers which complicate the chromatograms． the reaction is fast and the derivatives are stable． the fmoc derivatization method is five times more sensitivity than 2-aa derivatization method under the same conditions［33］．fmoc-cl was introduced to determinate the glucosamine sulfate in human plasma，the limit of detection was 15
ng /ml in hplc with a c18 column［34］． fmocderivatized glycans could be easily recovered as free glycans recoverable for functional studies in mild conditions with 20% piperidine in dmf at room temperaturel［35］． the recovery of free reducing oligosaccharides can be completed by incubation withmorpholine in dmf［33］． as fmoc-cl can also react with amino groups of peptide， the analysis of oligosaccharides may be interfered with peptides．
3 the fluorescence labeling of acidic sugars
3. 1 acidic sugars including sialic acid
the most significant feature of the sialylated glycans is their instability，where sialic acids ( sa)
would be destructed or released from sialylated glycans during ms procedures． the key advantage of this derivatization method is that the reaction conditions are mild． for incidence， in the labeling of sialooligosaccharides with 2-ab， the sialic acid was observed with no loss at 37 ℃ for 16 hours，however，significant loss of sialic acids can be observed at 65 ℃for 2 hours
1，2-diamino-4，5-methylenedioxybenzene ( dmb)possess significant advantages in its specific reactivity with the α-keto acids of sialic acids ( fig. 3 ) ．the derivatives showed strong fluorescence at 448 nm when excited at 373 nm． its application has been successfully in determining the n-acetylneuraminic acid ( neu5ac ) of human apoe by hplc with npropionylneuraminic acid as an internal standard［45］．
the neu5ac and n-glycolylneuraminic acid ( neu5gc) released from glycoproteins and glycolipids with dmb labeling were successfully separated on zorbax sb-aq columns and the limit of detection was 15. 6 pg for neu5ac and 5. 4 pg for neu5gc． in addition， the dmb reagent was found to be stable for up to 1 year at－ 20 ℃［46］． this method can be used for the labeling of streptococcus suis type 1， 1 /2， 4 capsular polysaccharides，and the ratio of sialic acid content t1，t1 /2，t14 was 1 ∶ 2. 7 ∶ 0. 2 ( based on our experimental data) ．
西安齐岳生物科技有限公司是国内较大的糖类衍生物，我们常年销售上百种糖化学衍生物试剂我们有氨基 炔烃 醛基 叠氮和荧光标记的各种结构的半乳糖 甘露糖 葡萄糖 纤维二糖 艾杜糖苷 壳聚二糖 岩藻糖 龙胆三糖 麦芽糖等不同产品。
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2-氟代-2-脱氧-1,3,5-三-o-乙酰基-α-d-呋喃阿拉伯糖444586-86-1
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荧光素-β-d-吡喃半乳糖苷 102286-67-9
荧光素-二-β-d-吡喃半乳糖苷 17817-20-8
荧光素-二-β-d-吡喃葡萄糖苷 129787-66-2
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荧光素-二-2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖苷
6-氟-3-吲哚基-β-d-吡喃半乳糖苷 207727-11-5
d-果糖-1，6-二磷酸三钠盐 81028-91-3
十七烷基-2-乙酰氨基-2-脱氧-β-d-吡喃葡糖苷 262856-90-6
十七烷基-2,3,4,6-四-氧-乙酰基-β-d-吡喃氨基葡萄糖苷
七烷基-2-乙酰氨基-2-脱氧-β-d-吡喃葡糖苷 20818-25-1
七烷基-2,3,4,6-四-氧-乙酰基-β-d-吡喃氨基葡萄糖苷 115431-24-8
庚烷基-β-d-吡喃葡萄糖苷 78617-12-6
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十六烷基-2-乙酰氨基-2-脱氧-β-d-吡喃葡糖苷 115414-49-8
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己基-2-乙酰氨基-2-脱氧-β-d-吡喃葡糖苷 190912-49-3
己基-2,3,4,6-四-氧-乙酰基-β-d-吡喃葡萄糖苷 172945-26-5
己基-β-d-吡喃葡糖苷 59080-45-4
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己基-β-d-硫代吡喃葡萄糖苷 85618-19-5
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2-氯-4-硝基苯基-β-d-麦芽三糖糖苷 165522-16-7
6'-(o-羧甲基)-2',7'-二氯荧光素 3'-(o-(n-乙酰基-β-d-葡萄糖苷))
3-羧基香豆素-β-d-吡喃葡萄糖醛酸 216672-17-2
3-羧基香豆素-β-d-吡喃半乳糖苷 64664-99-9
6-氯-3-吲哚基-2-乙酰氨基-2-脱氧-β-d-吡喃半乳糖苷 501432-61-7
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2-脱氧-d-葡萄糖 154-17-6
3-脱氧-d-葡萄糖 2490-91-7
1,2,;5,6-双-o-异亚丙基-a-d-呋喃阿洛糖
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十烷基-β-d-硫代吡喃葡萄糖苷 98854-16-1
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乙基-2,3,4,6-四-o-乙酰基-β-d-硫代吡喃半乳糖苷 55722-49-1
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乙基-1-硫代-β-d-吡喃半乳糖苷 7473-36-1
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2-氟代-2-脱氧-1,3,5-三-o-乙酰基-α-d-呋喃阿拉伯糖 444586-86-1
l-岩藻糖 2438-80-4
荧光素-β-d-吡喃半乳糖苷 102286-67-9
荧光素-二-β-d-吡喃半乳糖苷 17817-20-8
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d-果糖-1，6-二磷酸三钠盐 81028-91-3
十七烷基-2-乙酰氨基-2-脱氧-β-d-吡喃葡糖苷 262856-90-6
十七烷基-2,3,4,6-四-氧-乙酰基-β-d-吡喃氨基葡萄糖苷 585.77
七烷基-2-乙酰氨基-2-脱氧-β-d-吡喃葡糖苷 20818-25-1
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庚烷基-β-d-吡喃葡萄糖苷 78617-12-6
庚烷基-β-d-硫代吡喃葡萄糖苷 85618-20-8
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十六烷基-2,3,4,6-四-氧-乙酰基-β-d-吡喃氨基葡萄糖苷 115414-47-6
十六烷基-β-d-吡喃葡糖苷
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己基-2-乙酰氨基-2-脱氧-β-d-吡喃葡糖苷 190912-49-3
己基-2,3,4,6-四-氧-乙酰基-β-d-吡喃葡萄糖苷 172945-26-5
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己基-β-d-硫代吡喃葡萄糖苷 85618-19-5
4-甲基-6-十六酰氨基香豆素-β-d-吡喃半乳糖苷 94452-17-2
8-羟基喹啉基-β-d-吡喃半乳糖苷 113079-84-8
8-羟基喹啉基-β-d-吡喃葡萄糖苷 29266-96-4
8-羟基喹啉基-β-d-吡喃葡萄糖醛酸钠盐 207728-71-0
异丙基-2-乙酰氨基-3,4,6-三-o-乙酰基-2-脱氧-β-d-吡喃葡萄糖苷 7772-85-2
1,2-o-异亚丙基-α-d-呋喃葡萄糖苷 18549-40-1
i8001 吲哚-1,3-双醋酸盐 148565-57-5
i8004 3-吲哚基-β-d-吡喃半乳糖苷 126787-65-3
i8005 3-吲哚基-β-d-吡喃葡萄糖苷 487-60-5
i8006 3-吲哚基-β-d-吡喃葡萄糖醛酸
i8007 3 -吲哚基-β-d-吡喃葡萄糖醛酸环己铵盐 35804-66-1
i8008 3-吲哚基-β-d-吡喃葡萄糖醛酸钠盐 119736-51-5
i8009 3-吲哚基-2-乙酰氨基-2-脱氧-β-d-吡喃半乳糖苷
i8010 3-吲哚基-2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖苷
i8011 3-吲哚基-β-d-吡喃半乳糖苷-6-硫酸钠盐
i8012 5-碘-3-吲哚基-β-d-吡喃半乳糖苷
i8013 5-碘-3-吲哚基-β-d-吡喃半乳糖苷-6-硫酸钠盐
i8014 4-异硫氰基苯基-β-d-吡喃葡萄糖苷 20581-41-3
l8001 133310-19-7
m0001 4-甲氧基苯基-β-d-吡喃半乳糖苷 3150-20-7
m0002 4-甲氧基苯基-β-d-吡喃葡萄糖苷 6032-32-2
m0003 4-甲氧基苯基-2,3,4,6-四-o-乙酰基-β-d-吡喃半乳糖苷 2872-65-3
m0004 4-甲氧基苯基-2,3,4,6-四-o-乙酰基-β-d-吡喃葡萄糖苷 14581-81-8
m0005 4-甲氧基苯基-2,3,4,6-四-o-乙酰基-β-d-吡喃甘露糖苷 17042-40-9
m0006 4-甲氧基苯基-2,3,4,6-四-o-苄基-β-d-吡喃半乳糖苷 143536-99-6
m0007 甲基-2-乙酰氨基-2-脱氧-α-d-吡喃葡萄糖苷 6082-04-8
m0008 1-甲基-2-脱氧-d-核糖 60134-26-1
m0009 甲基-4,6-o-苯亚甲基-α-d-吡喃半乳糖苷 72904-85-9
m0010 甲基-4,6-o-苯亚甲基-β-d-吡喃半乳糖苷
m0016 甲基-2,3,4,6-四-o-苄基-α-d-吡喃半乳糖苷 53008-63-2
m0083 甲基2-乙酰胺基-2-脱氧-b-d-吡喃葡萄糖苷
m8011 4-甲基香豆素-2,3,4,6-四-o-乙酰基-α-d-吡喃甘露糖苷 28541-71-1
m8012 4-甲基香豆素-β-d-吡喃半乳糖苷 6160-78-7
m8013 4-甲基香豆素-β-d-吡喃葡萄糖苷 18997-57-4
m8014 4-甲基香豆素-α-d-吡喃甘露糖苷 28541-83-5
m8015 4-甲基香豆素-2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖苷 37067-30-4
m8017 4'-甲氧基-3,3',5-白藜芦醇-3-β-d-吡喃葡萄糖苷 155-58-8
m8018 n-甲基-3-吲哚基-β-d-吡喃半乳糖苷 207598-26-3
m8019 n-甲基-3-吲哚基-α-d-吡喃阿拉伯糖苷
m8020 4-甲基香豆素基-2-乙酰氨基-2-脱氧-3-氧-（α-l-吡喃岩藻糖基）-β-d-吡喃葡萄糖苷 383160-12-1
m8021 4-甲基香豆素基-2-乙酰氨基-2-脱氧-3，6-二-氧-特丁酰基-β-d-吡喃半乳糖苷
m8022 4-甲基香豆素基-2-乙酰氨基-2-脱氧-4-氧-（α-l-吡喃岩藻糖基）-β-d-吡喃葡萄糖苷 383160-13-2
m8023 4-甲基香豆素基-2-乙酰氨基-2-脱氧-6-氧-硫酸基-β-d-吡喃葡萄糖苷钾盐 210357-38-3
m8024 4-甲基香豆素基-2-乙酰氨基-2-脱氧-β-d-吡喃半乳糖苷 36476-29-6
m8025 4-甲基香豆素基-2-乙酰氨基-2-脱氧-β-d-吡喃半乳糖苷-4-硫酸基钾盐
m8026 4-甲基香豆素基-2-乙酰氨基-2-脱氧-β-d-吡喃半乳糖苷-6-硫酸基钾盐 383160-14-3
m8027 4-甲基香豆素基-2-脱氧-2-硫酸氨基-β-d-吡喃葡萄糖苷钠盐
m8028 4-甲基香豆素基-2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖苷-6-硫酸基钾盐 142439-99-4
m8029
m8030 4-甲基香豆素基-2-乙酰氨基-2-脱氧-3-氧-（β-d-吡喃半乳糖基）-α-d-吡喃半乳糖苷 210357-36-1
m8031 4-甲基香豆素基-2-乙酰氨基-3，4，6-三-氧-乙酰基-2-脱氧-α-d-吡喃葡萄糖苷
m8032 4-甲基香豆素基-2-乙酰氨基-3，4，6-三-氧-乙酰基-2-脱氧-β-d-吡喃半乳糖苷 124167-46-0
m8033 4-甲基香豆素基-2-乙酰氨基-3，4，6-三-氧-乙酰基-2-脱氧-β-d-吡喃葡萄糖苷 124167-45-9
m8034 4-甲基香豆素基-2-氨基-2-脱氧-α-d-吡喃葡萄糖苷 137687-00-4
m8035 4-甲基香豆素基-2-脱氧-2-硫酸氨基-α-d-吡喃葡萄糖苷钠盐 180088-52-2
m8036 4-甲基香豆素基-2-氧-（2，3，4-三-氧-苯甲酰基-α-l-吡喃岩藻糖基）-β-d-吡喃半乳糖苷
m8037 4-甲基香豆素基-2-氧-（α-l-吡喃岩藻糖基）-β-d-吡喃半乳糖苷 225217-42-5
m8038 4-甲基香豆素基-2，3-二-氧-苯甲酰基-4，6-氧-苄叉基-β-d-吡喃半乳糖苷
m8039 4-甲基香豆素基-2,3,4,6-四-氧-乙酰基-α-d-吡喃葡萄糖苷 67945-53-3
m8040 4-甲基香豆素基-2,3,6-三-氧-苯甲酰基-β-d-吡喃葡萄糖苷
m8041 c21h24nnao11
m8042 4-甲基香豆素基-3-氧-（α-l-吡喃岩藻糖基）-β-d-吡喃半乳糖苷 296776-06-2
m8043 4-甲基香豆素基-3，4，6-三-氧-乙酰基-2-脱氧-2-三氟乙酰氨基-β-d-吡喃葡萄糖苷 137686-93-2
m8044 4-甲基香豆素基-3，4，6-三-氧-乙酰基-2-脱氧-2-三氟乙酰氨基-β-d-吡喃葡萄糖苷 137686-93-2
m8045 4-甲基香豆素基-3,4,6-三-氧-乙酰基-2-氧-（2，3，4-三-氧-苯甲酰基-α-l-吡喃岩藻糖基）-β-d-吡喃葡萄糖苷
m8046 4-甲基香豆素基-3,4,6-三-氧-乙酰基-β-d-吡喃半乳糖苷
m8047 4-甲基香豆素基 4-脱氧壳聚二糖
m8048 4-甲基香豆素基-4-氧-（α-l-吡喃岩藻糖基）-β-d-吡喃半乳糖苷 383160-15-4
m8049 4-甲基香豆素基-4，6-氧-苄叉基-β-d-吡喃半乳糖苷
m8050 4-甲基香豆素基-6-硫-十六酰基-β-d-吡喃葡萄糖苷 229644-17-1
m8051 4-甲基香豆素基-α-d-吡喃阿拉伯糖苷
m8052 4-甲基香豆素基-α-d-吡喃半乳糖苷 38597-12-5
m8053 4-甲基香豆素基-α-d-吡喃葡萄糖苷 17833-43-1
m8054 4-甲基香豆素基-4,7,8,9-四-氧-乙酰基-α-d-唾液酸甲酯 59361-08-9
m8055 4-甲基香豆素基-α-l-呋喃阿拉伯糖苷 77471-44-4
m8056 4-甲基香豆素基-α-l-吡喃阿拉伯糖苷 69414-26-2
m8057 4-甲基香豆素基-α-l-吡喃岩藻糖苷 54322-38-2
m8058 4-甲基香豆素基-α-l-吡喃艾杜糖醛酸-2-硫酸钠盐 1045020-74-3
m8059 4-甲基香豆素基-α-l-吡喃艾杜糖苷 66901-41-5
m8060 4-甲基香豆素基-α-l-吡喃艾杜糖醛酸环己铵盐 66895-33-8
m8061 4-甲基香豆素基-α-l-吡喃艾杜糖醛酸钠盐 89157-94-8
m8062 4-甲基香豆素基-β-d-纤维二糖苷 72626-61-0
m8063 4-甲基香豆素基-β-d-纤维三糖苷
m8064 4-甲基香豆素基 全乙酰化壳聚二糖
m8065 4-甲基香豆素基-β-d-吡喃岩藻糖苷 55487-93-9
m8066 4-甲基香豆素基-β-d-吡喃半乳糖苷-6-硫酸 126938-14-5
m8067 4-甲基香豆素基-β-d-吡喃半乳糖苷-6-硫酸钠盐 206443-06-3
m8068 4-甲基香豆素基-β-d-龙胆三糖苷 383160-16-5
m8069 4-甲基香豆素基-β-d-吡喃葡萄糖醛酸（一水合） 6160-80-1
m8070 4-甲基香豆素基-β-d-吡喃葡萄糖醛酸（三水合） 199329-67-4
m8071 4-甲基香豆素基-β-d-吡喃乳糖苷 84325-23-5
m8072 4-甲基香豆素基-β-d-吡喃甘露糖苷 67909-30-2
m8073 4-甲基香豆素基-β-d-呋喃阿拉伯糖苷 195385-93-4
m8074 4-甲基香豆素基-β-d-吡喃木糖苷 195385-93-4
m8075 4-甲基香豆素基-β-l-吡喃阿拉伯糖苷
m8076 4-甲基香豆素基-β-l-吡喃岩藻糖苷 72601-82-2