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Cracking connecting unit for tetrahydrofuran ether derivatives and application of cracking connecting unit

A technology of tetrahydrofuran ether and linking units, which is applied in the fields of chemical synthesis and biochemistry, can solve problems such as insufficient mild cracking conditions, low cracking efficiency, and short read length, and achieve high-efficiency cracking effects

Active Publication Date: 2012-09-19
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these linking units have their own disadvantages and limitations (Bioorganic & Medicinal Chemistry 2012, 20, 571-582)
[0005] The cleavable junction unit has an important impact on the read length and efficiency of sequencing by synthesis. However, the existing junction unit has disadvantages such as insufficient cleavage conditions, low cleavage efficiency, and too short read length for sequencing. Therefore, the design, Synthesizing new cleavable junction units and exploring suitable cleavage conditions are of great significance for improving the efficiency of sequencing and developing new sequencing methods

Method used

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  • Cracking connecting unit for tetrahydrofuran ether derivatives and application of cracking connecting unit
  • Cracking connecting unit for tetrahydrofuran ether derivatives and application of cracking connecting unit
  • Cracking connecting unit for tetrahydrofuran ether derivatives and application of cracking connecting unit

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1, when n=0, the synthesis of connecting unit T-8

[0064] The schematic diagram of the synthetic route of linking unit T-8 (5-hydroxymethyl-2-(2-aminoethoxy)-tetrahydrofuran) is as follows figure 1 As shown, the synthesis steps are as follows:

[0065] (1) Synthesis of T-1: D, L or DL-glutamic acid is reacted in the presence of sodium nitrite to obtain T-1.

[0066] The steps are as follows: add 10 g (68 mmol) of D, L or DL-glutamic acid into a 500 mL single-necked bottle, add hydrochloric acid (14 mL of concentrated hydrochloric acid dissolved in 28 mL of water), and dissolve the solid. Stir in an ice bath for 30 min, then continue to add a solution of sodium nitrite (7 g, 100 mmol, dissolved in 30 mL of water) dropwise in an ice bath, during which reddish-brown smoke is produced. After the dropwise addition, the reaction was continued for 3 h in an ice bath, and then moved to room temperature overnight. The water was distilled off under reduced pressu...

Embodiment 2

[0088] Embodiment 2, when n=2, the synthesis of connecting unit T-8'

[0089] The schematic diagram of the synthetic route is as figure 2 As shown, the synthesis steps are as follows:

[0090] (1) The synthesis of T-1 to T-4 is the same as that described in Example 1.

[0091] (2) Synthesis of T-6': T-4 reacts with bromotriethylene glycol to obtain T-6'.

[0092] The specific steps are: take 232mg T-4 (1mmol), add 15mL dichloromethane to dissolve, add 426mg monobromotriethylene glycol (2mmol), add 50mg Amberlyst A-15, add reflux at 50°C for 2h. Stop the reaction, remove A-15 by filtration, and wash with saturated sodium bicarbonate and saturated brine. The solvent was distilled off under reduced pressure to obtain 600 mg of light yellow oily liquid. Packed with silica gel column, petroleum ether: ethyl acetate = 5: 1 column separation to obtain 128 mg of light green T-6' pure product with a yield of 30%. Cis: 1 H NMR (CDCl 3 , 400M): δ5.17(1H, d, J=4.8Hz), 4.17~4.08(...

Embodiment 3

[0098] Embodiment 3, when n=44, the synthesis of linking unit T-8 "

[0099] The schematic diagram of the synthetic route is as image 3 As shown, the synthesis steps are as follows:

[0100] (1) The synthesis of T-1 to T-4 is the same as that described in Example 1.

[0101] (2) Synthesis of T-6 ": T-4 reacts with brominated polyethylene glycol 2000 to obtain T-6".

[0102] The steps are as follows: take 1 mmol of T-4, add 15 mL of dichloromethane to dissolve, add 2 mmol of monobrominated polyethylene glycol 2000, add 50 mg of Amberlyst A-15, add reflux at 50°C for 2 hours. Stop the reaction, remove A-15 by filtration, and wash with saturated sodium bicarbonate and saturated brine. The solvent was distilled off under reduced pressure to obtain 600 mg of light yellow oily liquid. Packed on a silica gel column and separated with petroleum ether: ethyl acetate = 5:1 column to obtain 213 mg of light green T-6" pure product. 1 H NMR (CDCl 3 , 400M): δ5.19(1H, d, J=4.8Hz), ...

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PUM

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Abstract

The invention discloses a cracking connecting unit for tetrahydrofuran ether derivatives and application of the cracking connecting unit. The cracking connecting unit has the following structural formula, wherein n is any integer of 0 to 44. The cis-tetrahydrofuran ether derivatives, the trans-tetrahydrofuran ether derivatives or the cis- and trans-tetrahydrofuran ether derivatives can be used for sequencing, and have the same effect; the synthesizing raw materials for the compounds are simple and readily available, the synthesizing process is conventional chemical reaction, and massive synthesis is easy to realize; the compounds can be efficiently connected with nucleotide and fluorescein; and by researching the cracking performance of the compounds, the compounds can realize efficient cracking under mild conditions, and can be applied to DNA sequencing.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and biochemistry, in particular to a tetrahydrofuran ether derivative cleavable linking unit that can be used for DNA synthesis sequencing and its use. Background technique [0002] DNA sequencing technology is one of the important means in modern biological research. After the completion of the Human Genome Project, DNA sequencing technology has developed rapidly. DNA sequencing (DNA sequencing) refers to the analysis of the base sequence of a specific DNA fragment, that is, the arrangement of adenine (A), thymine (T), cytosine (C) and guanine (G). The development of accurate, high-throughput, and low-cost DNA sequencing methods is of great significance to biological and medical sciences. [0003] Sequencing By Synthesis (SBS) is one of the next-generation DNA sequencing technologies. The synthetic sequencing method immobilizes a large number of template DNA fragments to be tested, hybridize...

Claims

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Application Information

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IPC IPC(8): C07D307/20C08G65/48C12Q1/68
CPCY02P20/55
Inventor 沈玉梅庄园郭勋祥伍新燕邵志峰龚兵黎庆
Owner SHANGHAI JIAO TONG UNIV
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