关于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 neutralsugars，the labelingreaction which targets the lone electronpair of amino groups of reducing sugarsis effective for the labeling to the carbon of carbonyl groups ( Fig. 1) ．The common fluorescence labels are2-aminopyridine，aminobenzene，aminonaphthalene sulfonic acidisomers and hydrazines．

2 The fluorescence labeling of amino sugars

The amino sugars have been extensivelypresent in plants and animals． The amino groups or acetyl amino groups in sugars provide theopportunity for coupling reactions to form derivatives．

A novel sensitive fluorescent label of9-fluorenylmethoxy chloroformate ( Fmoc-Cl) can readily

react with amino groups in sugars． Fmoc sugar derivatives have aunique configuration ( i． e． ，β-form) at the reducing end，and have no isomers which complicatethe chromatograms． The reactionis fast and the derivatives are stable． The Fmoc derivatization method is five times more sensitivity than2-AA derivatization method under the same conditions［33］．Fmoc-Cl was introduced to determinate the glucosamine sulfate inhuman plasma，the limit ofdetection was 15

ng /mL in HPLC with a C18 column［34］． Fmocderivatized glycans could be easily recovered as free glycansrecoverable for functional studies in mild conditions with 20% piperidine inDMF at room temperaturel［35］． Therecovery of free reducing oligosaccharides can be completed by incubationwithmorpholine in DMF［33］． As Fmoc-Clcan also react with amino groups of peptide， the analysis of oligosaccharides may be interfered with peptides．

3 The fluorescence labeling of acidicsugars

3. 1 Acidic sugars including sialic acid

The most significant feature of the sialylatedglycans is their instability，where sialic acids ( SA)

would be destructed or released fromsialylated glycans during MS procedures． The key advantage of this derivatization method is that thereaction conditions are mild． For incidence， in the labeling of sialooligosaccharides with 2-AB， the sialic acid was observed withno loss at 37 ℃ for 16 hours，however，significant loss of sialic acidscan be observed at 65 ℃for 2 hours

1，2-Diamino-4，5-methylenedioxybenzene ( DMB)possess significant advantages in itsspecific reactivity with the α-keto acids of sialic acids ( Fig. 3 ) ．The derivatives showed strongfluorescence at 448 nm when excited at 373 nm． Its application has been successfully in determining theN-acetylneuraminic acid ( Neu5Ac ) of human apoE by HPLC withNpropionylneuraminic acid as an internal standard［45］．

The Neu5Ac and N-glycolylneuraminic acid (Neu5Gc) released from glycoproteins and glycolipids with DMB labeling weresuccessfully separated on Zorbax SB-Aq columns and the limit of detection was15. 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 methodcan 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 ( basedon 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

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

荧光素-二-β-D-吡喃葡萄糖苷   129787-66-2

荧光素-二-β-D-吡喃葡萄糖醛酸甲酯      

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

庚烷基-β-D-硫代吡喃葡萄糖苷        85618-20-8

十六烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷      115414-49-8

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

十六烷基-β-D-麦芽糖苷    98064-96-1

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

己基-β-D-麦芽糖苷    870287-95-9

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

烯丙基-2,3-二-O-苄基-a-D-吡喃葡萄糖苷

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烯丙基-D-葡萄糖醛酸盐     

2-乙酰胺基-3,4,6-三-O-乙酰基-2-脱氧-b-D-吡喃葡萄糖 三氯乙酰亚胺酯  

4-氨基苯基-β-D-吡喃半乳糖苷 5094-33-7

4-氨基苯基-β-D-吡喃葡萄糖苷 20818-25-1

4-氨基苯基-β-D-吡喃岩藻糖苷 69936-58-9

5-乙酰氨基荧光素-二-β-D-半乳糖苷       216299-45-5

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N-(12-氨十二酰基)-1-脱氧野尻霉素  885484-41-3

4-氨基苯基-α-D-吡喃葡萄糖苷 31302-52-0

4-氨基苯基-β-D-吡喃纤维二糖苷     42935-24-0

4-氨基苯基-β-D-吡喃乳糖苷     17691-02-0

对羟基苯基-β-D-吡喃葡萄糖苷 497-76-7

4-氨基苯基-1-硫代-β-D-半乳糖苷    29558-05-2

4,6-O-苯亚甲基-D-半乳糖   3006-41-5

4,6-O-苯亚甲基-D-葡萄糖   30688-66-5

苄基-2-乙酰氨基-2-脱氧-3,4,6-三-O-乙酰基-α-D-吡喃葡萄糖     

丁烷基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖  155197-37-8

丁烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖   25320-93-8

丁烷基-α-D--吡喃葡萄糖   25320-93-8

苄基-2,3,4,6-四-O-乙酰基-b-D-吡喃葡萄糖苷  

5-溴-3-吲哚-β-D-吡喃半乳糖苷 97753-82-7

5-溴-3-吲哚-磷酸酯对甲苯胺盐  80008-69-1

5-溴-4-氯-3-吲哚-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷     210110-89-7

5-溴-4-氯-3-吲哚-2-乙酰氨基-2-脱氧-β-D-吡喃半乳糖苷     129572-48-1

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5-溴-4-氯-3-吲哚-α-L-吡喃岩藻糖苷       171869-92-4

5-溴-4-氯-3-吲哚-β-D-吡喃葡萄糖苷       15548-60-4

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5-溴-4-氯-3-吲哚-β-D-纤维二糖糖苷       177966-52-8

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5-溴-6-氯-3-吲哚-α-L-吡喃岩藻糖苷      

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6-溴-2-萘基 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷     

6-溴-2-萘基 α-D-吡喃半乳糖苷       25997-59-5

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6-溴-2-萘基 α-D-吡喃甘露糖苷       28541-84-6

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6-溴-2-萘基 β-D-吡喃葡萄糖醛酸    22720-35-0

6-溴-2-萘基 β-D-吡喃木糖苷    69594-75-8

5-溴-4-氯-3-吲哚基-α-D-吡喃葡萄糖苷   108789-36-2

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5-溴-4-氯-3-吲哚基-α-L-呋喃阿拉伯糖苷      

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5-溴-3-吲哚基-β-D-吡喃糖醛酸环己铵盐 18656-96-7

5-溴-3-吲哚基-β-D-吡喃葡萄糖苷   

5-溴-3-吲哚基-β-D-吡喃半乳糖苷-6-硫酸钠盐      

5-溴-3-吲哚基-α-D-吡喃甘露糖苷   

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5-溴-3-吲哚基 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷  58225-98-2

5-溴-4-氯-3-吲哚基-α-D-吡喃木糖苷      

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5-溴-4-氯-3-吲哚基-β-D-吡喃甘露糖苷   129787-67-3

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5-溴-4-氯-3-吲哚基-β-L-吡喃岩藻糖苷    125328-84-9

5-溴-4-氯-3-吲哚基 正壬酸酯    133950-77-3

5-溴-4-氯-3-吲哚基 磷酸二钠盐 102185-33-1

5-溴-4-氯-3-吲哚磷酸酯 对甲苯铵盐 1708-76-6

5-溴-4-氯-3-吲哚基 硫酸钾盐    6578-07-0

5-溴-4-氯-3-吲哚基-β-D-吡喃葡萄糖醛酸       144110-42-9

5-溴-6-氯-3-吲哚基-β-D-吡喃葡萄糖醛酸环己铵盐       144110-43-0

5-溴-6-氯-3-吲哚基 磷酸对甲苯铵盐 6769-80-8

5-溴-4-氯-3-吲哚辛酸酯     

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

6-氯-3-吲哚基-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷   156117-44-1

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6-氯-3-吲哚基-α-D-吡喃葡萄糖苷    467214-46-6

6-氯-3-吲哚基-α-D-吡喃甘露糖苷    425427-88-9

6-氯-3-吲哚基-β-D-吡喃纤维二糖苷 425427-87-8

4-氯-3-吲哚基-β-D-吡喃半乳糖苷    135313-63-2

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6-氯-3-吲哚基-β-D-吡喃葡萄糖醛酸环己铵盐 138182-20-4

6-氯-3-吲哚基-β-D-吡喃葡萄糖醛酸钠盐 216971-56-1

6-氯-3-吲哚基 磷酸对甲苯铵盐  159954-33-3

2-氯-4-硝基苯基-2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖苷     

2-氯-4-硝基苯基-2,3,4,6-四-氧-乙酰基-α-D-吡喃葡萄糖苷   153823-58-6

2-氯-4-硝基苯基-2,3,4,6-四-氧-乙酰基-β-D-吡喃葡萄糖苷   35023-71-3

2-氯-4-硝基苯基 α-D-吡喃岩藻糖苷      

2-氯-4-硝基苯基-α-D-吡喃葡萄糖苷 119047-14-2

2-氯-4-硝基苯基-α-D-吡喃麦芽三糖苷    118291-90-0

2-氯-4-硝基苯基-α-L-吡喃岩藻糖苷 157843-41-9

2-氯-4-硝基苯基-β-D-吡喃纤维二糖苷    135743-28-1

2-氯-4-硝基苯基-β-D-吡喃半乳糖苷 123706-60-5

2-氯-4-硝基苯基-β-D-吡喃乳糖苷    120583-41-7

2-氯-4-硝基苯基-β-D-麦芽三糖糖苷 165522-16-7

4-氯甲基-6，8-二氟香豆素-β-D-吡喃半乳糖苷      215868-46-5

氯苯酚红-β-D-吡喃半乳糖苷    99792-79-7

氯苯酚红-β-D-吡喃半乳糖苷钠盐   

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  

2-脱氧-L-核糖       18546-37-7

十二烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷      147025-06-7

十烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷   147025-05-6

十烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷   135198-04-8

十烷基-a-D-麦芽糖苷   168037-12-5

十烷基-β-D-吡喃葡萄糖苷 58846-77-8

十烷基-b-D-麦芽糖苷   82494-09-5

十烷基-β-D-硫代吡喃葡萄糖苷 98854-16-1

十一烷基-β-D-硫代麦芽糖苷    14565-56-4

2,6-二甲基-4-庚基 -b-D-麦芽糖苷     869638-31-3

十二烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷       211567-22-5

十二烷基-a-D-吡喃葡萄糖苷      29980-16-3

十二烷基-a-D-麦芽糖苷      116183-64-3

十二烷基-β-D-吡喃葡萄糖苷    59122-55-3

十二烷基-β-D-麦芽糖苷    69227-93-6

十二烷基-β-D-硫代麦芽糖苷    148565-58-6

十二烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷   49810-41-5

十二烷基-β-D-吡喃半乳糖苷    2495-96-7

4-甲基-6，8-二氟香豆素-β-D-吡喃葡萄糖苷  351009-26-2

5-十二酰氨基荧光素-二-β-D-吡喃半乳糖苷    138777-25-0

乙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-α-D-硫代葡萄糖苷  49810-41-5

乙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖苷  76155-50-5

乙基-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷   2495-96-7

乙基-2,3,4,6-四-O-乙酰基-α-D-硫代吡喃半乳糖苷 126187-25-5

乙基-2,3,4,6-四-O-乙酰基-α-D-硫代吡喃葡萄糖苷 56245-73-5

乙基-2,3,4,6-四-O-乙酰基-β-D-硫代吡喃半乳糖苷 55722-49-1

乙基2,3,4,6-四-O-乙酰基-β-D-硫代吡喃葡萄糖苷 4160-79-5

乙基-1-硫代-β-D-吡喃半乳糖苷       7473-36-1

乙基-1-硫代-β-D-吡喃半乳糖苷       56245-60-4

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

荧光素-二-β-D-吡喃葡萄糖苷   129787-66-2

荧光素-二-β-D-吡喃葡萄糖醛酸甲酯      

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       585.77

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

庚烷基-β-D-硫代吡喃葡萄糖苷 85618-20-8

十六烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷      115414-49-8

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

十六烷基-β-D-麦芽糖苷    98064-96-1

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

己基-β-D-麦芽糖苷    870287-95-9

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