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Synthetic route for antibiotic teixobactin and analogs thereof

A solid-phase synthesis, fmoc-l-technology, applied in the preparation method of peptides, organic chemistry, peptides, etc., can solve the problems of difficulty in the total synthesis of teixobactin, complex structure, etc., and achieve the effect of less by-products and high esterification efficiency

Active Publication Date: 2019-02-12
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, L-allo-Enduracidine (End) unnatural amino acid plays an important role in antibacterial activity, but its structure is complex, and there is no relatively simple synthesis strategy at present, and the total synthesis of teixobactin is more difficult

Method used

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  • Synthetic route for antibiotic teixobactin and analogs thereof
  • Synthetic route for antibiotic teixobactin and analogs thereof
  • Synthetic route for antibiotic teixobactin and analogs thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0143]

[0144] Synthesis of compound shown in formula 2:

[0145] Add the compound (10mmol) shown in Formula 1 into a round bottom flask, add 20ml of acetonitrile, add solid sodium bicarbonate (40mmol) and stir at zero, slowly add elemental iodine (30mmol) and stir for one hour, then spin dry the acetonitrile; Next, add acetic acid and methanol mixed solution (acetic acid: methanol / 1:9) and stir at room temperature for 15 minutes, then spin off the methanol, wash with aqueous sodium bicarbonate and separate through silica gel column (dichloromethane: methanol / 20:1) to obtain the target Product, yield 71%. 1 H NMR (400MHz, DMSO) δ (ppm) 7.90-7.88 (d, J = 7.48Hz, 2H), 7.82-7.80 (d, J = 7.8Hz, 1H), 7.71-7.69 (m, 2H), 7.43- 7.31(m,8H),5.21(s,2H),4.36-4.26(m,3H),4.22-4.21(m,1H),3.97-3.92(t,J=9.48Hz,1H),3.87-3.80( m,1H),3.62(s,3H),3.51-3.47(m,1H),1.86-1.82(m,2H).13C NMR(400MHz,DMSO)δ172.82,156.07,152.86,151.95,143.74,142.56,140.73 ,139.41,137.41,135.61,128.92,128.48,128.39,12...

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Abstract

The invention discloses a synthetic route for antibiotic teixobactin and analogs thereof and a method for preparing unnatural amino acids. The method comprises: subjecting a compound shown in a formula (1) to oxidative ring-closing treatment. In the formula, R5 is independently Fmoc, Boc, Phth, or Cbz, and R6 is independently H, Fmoc, Boc, Phth, or Cbz. The method was first proposed by the inventors. By using the oxidative ring-closing reaction, L-allo-Enduracidine (End) unnatural amino acids can be obtained in one step. The method has high yield, few by-products, and simple separation and purification.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, specifically, the present invention relates to the preparation method of novel antibiotics for the treatment of drug-resistant Gram-positive bacteria and tuberculosis, more specifically, the present invention relates to the synthetic route of antibiotic teixobactin and its analogues. Background technique [0002] Gram-positive bacterial infection is a common and frequently-occurring disease that endangers human health. In recent years, Gram-positive cocci infections have increased day by day, the detection rate of methicillin-resistant Staphylococcus aureus (MRSA) has increased, penicillin-resistant Streptococcus pneumoniae (PRSP) has spread in many countries and regions, glycopeptide-resistant and other Antibiotic vancomycin-resistant enterococci (VRE) appeared, and multidrug-resistant Mycobacterium tuberculosis continued unabated. In order to effectively control the antibiotic-resist...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/04C07K1/06C07D233/46C07D233/48
CPCC07D233/46C07D233/48C07K7/06
Inventor 饶燏宗昱
Owner TSINGHUA UNIV
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