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Process for synthesizing ergothioneine and related compounds

A kind of technology of ergothioneine and compound, applied in the field of synthesizing ergothioneine and related compounds, can solve problems such as high cost

Active Publication Date: 2017-08-29
UNIVERSITY OF CAPE TOWN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, known synthetic methods for the synthesis of ESH can only achieve low to moderate yields at very high cost

Method used

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  • Process for synthesizing ergothioneine and related compounds
  • Process for synthesizing ergothioneine and related compounds
  • Process for synthesizing ergothioneine and related compounds

Examples

Experimental program
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Embodiment

[0139] 1. General procedure

[0140] All solvents were dried by appropriate techniques and freshly distilled before use. All commercially available reagents were purchased from Sigma-Aldrich and Merck and used without further purification.

[0141] Unless otherwise stated, the reactions were carried out in oven-dried glassware under an inert atmosphere of nitrogen, and the 254 Thin layer chromatography (TLC) monitoring performed on precoated plates (0.2 mm layer), product visualized under UV light at 254 nm or by spraying the plate with ninhydrin (2% v / v) in ethanol and then visualized by heating .

[0142] Column chromatography was performed by using Merck Kieselgel silica gel 60 (0.040mm-0.063mm) and eluted with a suitable solvent mixture. All compounds were dried under vacuum before determining their yields.

[0143] Unless otherwise stated, NMR spectra ( 1 H and 13 C) Recorded at Varian Mercury 300MHz (75MHz, 13 C), Varian Unity 400MHz (101MHz, 13 C), Bruker unity ...

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Abstract

The invention provides a process for synthesising a compound of formula (V) wherein: formula (z) or a physiologically acceptable salt, tautomer, stereoisomer or mixture of stereoisomers thereof. The process utilizes a / V-benzyl protected histidine rather than the unprotected form of histidine. The process of the invention comprises the steps of: (a) deprotecting a / V-benzyl protected histidine of formula 11 to form A / -benzyl histidine of formula 12; (b) converting compound 12 to (S)-3-(1 -benzyl-1 H-imidazol-4-yl)-2-(dimethylamino)propanoic acid of formula 13; (c) converting compound 13 to (2S)-N,N,N-2-trimethylethanaminium-3-(1 -benzyl- 1H-imidazol-4-yl)propanoic acid of formula 14; (d) brominating the imidazole ring of the compound of formula 14 to form 5-bromohercynine lactone (reactive intermediate); and (e) converting the 5-bromohercynine lactone of step (d) to (p-amino-p- carboxyethyl)ergothioneine sulfide of formula 15. The process optionally further includes one of steps (f) to (h): (f) converting the compound of formula 15 to a sulfoxide; (g) converting the compound of formula 15 to a sulfone; or (h) converting the compound of formula 15 to ergothioneine (ESH).

Description

technical field [0001] Methods for the synthesis of ergothioneine and related compounds of formula V are described. Background technique [0002] Many Gram-positive bacteria, such as Mycobacterium tuberculosis, produce ergothioneine (ESH) as a protective small molecule thiol. 1,2,3 ESH is a thiohistidine betaine derivative with a thiol group at the C2 atom (ε position) of the imidazole ring (Scheme 1). Recently, it was discovered that ESH is transmitted by Mycobacterium smegmatis 4 Actively secreted into the culture medium, and existing knowledge suggests that ESH may play a critical role in the survival of mycobacteria in vivo and in vitro. [0003] A structural variant of ESH, ovothiol A, also acts as an antioxidant in sea urchin eggs and the pathogens Leishmania major and Trypanosoma cruzi 5 . [0004] Humans do not synthesize ESH but have an active transport system, a highly specific cation transporter (OCTN1), which ingests it from dietary sources 6,7 . [0005] I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/84
CPCC07D233/84A61K31/4164
Inventor M·A·加尔迪内L·P·孔德
Owner UNIVERSITY OF CAPE TOWN
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