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United States Patent (10 ) Patent No.: US 10,538,797 B2 Thomsen Et Al

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United States Patent (10 ) Patent No.: US 10,538,797 B2 Thomsen Et Al US010538797B2 United States Patent (10 ) Patent No.: US 10,538,797 B2 Thomsen et al. (45 ) Date of Patent : Jan. 21 , 2020 (54 ) METHOD FOR THE BIOTECHNOLOGICAL ( 56 ) References Cited PRODUCTION OF FLAVONE GLYCOSIDE DIHYDROCHALCONES U.S. PATENT DOCUMENTS 9,359,622 B2 * 6/2016 Hilmer C12Y 505/01006 (71 ) Applicant: SYMRISE AG , Holzminden (DE ) 2014/0045233 A1 * 2/2014 Hilmer C12Y 505/01006 435/148 ( 72 ) Inventors : Maren Thomsen , Greifswald (DE ) ; Jakob Ley , Holzminden ( DE ) ; Egon FOREIGN PATENT DOCUMENTS Gross , Holzminden (DE ); Winfried Hinrichs , Greifswald (DE ) ; Uwe EP 2 692 729 A1 2/2014 Bornscheuer, Greifswald (DE ) OTHER PUBLICATIONS ( 73 ) Assignee : SYMRISE AG , Holzminden (DE ) Accession V9P0A9 . Mar. 19 , 2014. Alignment to SEQ ID No. 2 ( Year: 2014 ). * ( * ) Notice : Subject to any disclaimer, the term of this Accession V9P0A9 . Mar. 19 , 2014. Alignment to SEQ ID No. 4 ( Year: 2014 ). * patent is extended or adjusted under 35 Accession KF154734 . Dec. 31, 2013. Alignment to SEQ ID No. 1 . U.S.C. 154 ( b ) by 16 days . ( Year: 2013 ) . * Accession KF154734 . Dec. 31, 2013. Alignment to SEQ ID No. 3 . ( 21 ) Appl. No.: 15 /322,768 ( Year : 2013 ) . * Chica et al. Curr Opin Biotechnol . Aug. 2005; 16 ( 4 ): 378-84 . ( Year : 2005 ) . * ( 22 ) PCT Filed : Jun . 27 , 2015 Singh et al . Curr Protein Pept Sci. 2017 , 18 , 1-11 ( Year: 2017) . * Bornscheuer et al. Curr Protoc Protein Sci. Nov. 2011; Chapter PCT No .: PCT/ EP2015 / 064626 26 :Unit26.7 . ( Year: 2011 ). * ( 86 ) Gall et al, “ Enzymatische Umsetzung von Flavonoiden mit einer $ 371 ( c ) ( 1 ) , backteriellen Chalconisomerase und einer Enoatreduktase ,” Angewandte ( 2 ) Date : Apr. 6 , 2018 Chemie vol. 126 , No. 5 , Jan. 27 , 2014 , pp . 1463-1466 . ( 87 ) PCT Pub . No .: WO2016 /012198 * cited by examiner Primary Examiner — Christian L Fronda PCT Pub . Date : Jan. 28 , 2016 ( 74 ) Attorney , Agent, or Firm - Polsinelli PC (65 ) Prior Publication Data (57 ) ABSTRACT The invention relates to method for producing flavone US 2018/0216152 A1 Aug. 2 , 2018 glycoside dihydrochalcones, having the following steps : ( a ) providing a transgenic microorganism containing (i ) a first (30 ) Foreign Application Priority Data nucleic acid portion ( A ) containing a gene which codes for a bacterial chalcone isomerase and ( ii ) a second nucleic acid Jul . 1 , 2014 (EP ) 14175312 portion ( B ) containing a gene which codes for a bacterial enoate reductase , (b ) adding one or more flavone glycosides to the transgenic microorganism under conditions which ( 51 ) Int. Cl. allow the simultaneous isomerization and reduction of the C12P 19/60 ( 2006.01 ) flavone glycoside into the flavone glycoside dihydrochal C12P 17/06 ( 2006.01) cone, and optionally ( d ) isolating and purifying the final A23L 2730 ( 2016.01 ) product, wherein the nucleic acid portion ( A ) ( 1 ) is a ( 52 ) U.S. CI. nucleotide sequence according to SEQ ID NO : 1 , in which CPC C12P 19/605 (2013.01 ) ; A23L 27/33 the nucleic acid portion ( A ') according to SEQ ID NO : 3 has (2016.08 ) ; C12P 17/06 ( 2013.01) ; C12Y been cut out, or ( 2 ) is an amino acid sequence according to 103/01031 (2013.01 ) ; C12Y 505/01006 SEQ ID NO : 2 , in which the amino acid portion ( A ') accord ( 2013.01 ) ing to SEQ ID NO : 4 has been cut out. ( 58 ) Field of Classification Search None 12 Claims, 2 Drawing Sheets See application file for complete search history. Specification includes a Sequence Listing . U.S. Patent Jan. 21 , 2020 Sheet 1 of 2 US 10,538,797 B2 PET28b CHI deltaLid 6,028 bp COE1 BR322 origin Figure 1 Plasmide PET28_CHI_ALid . U.S. Patent Jan. 21 , 2020 Sheet 2 of 2 US 10,538,797 B2 soluble fraction Unsoluble Fraction On 2h 21h 2h 4h 21h Oh 65 kea ERED 43 kDa 27 Kba CHI_ALid Figure 2 SDS- PAGE of the expression of the double transformation of PET22_ERED and PET28_CHI ALid . Oh denotes the time point of the induction . Conversion1%) 40 Naringenin Naringin 4h Naringin 22h Figure 3 Conversion of the substrates by means of whole -cell - catalysis . US 10,538,797 B2 1 2 METHOD FOR THE BIOTECHNOLOGICAL derivative or derivatives thereof to a dihydrochalcone, as PRODUCTION OF FLAVONE GLYCOSIDE well as optionally : isolating and optionally purifying the DIHYDROCHALCONES dihydrochalcone, in particular phloretin . The paper by Gall et al. having the title “ Enzymatic CROSS -REFERENCE TO RELATED 5 conversion of flavonoids with a bacterial chalcone APPLICATIONS isomerase and an enoate reductase ” (Angewandte Chemie , 2014 , 126 ( 5 ) , pp . 1463-1466 ) describes the identification This application is a national stage application (under 35 and the recombinant expression of chalcone isomerase and U.S.C. § 371 ) of PCT/ EP2015 / 064626 , filed Jun . 27, 2015 , an enoate reductase from the anaerobic bacterium Eubacte which claims benefit of European Application No. 10 rium ramulus . The E. coli strain expressing the two enzymes 14175312.9 , filed Jul. 1 , 2014 , which are incorporated can be used to carry out the conversion of various flavanones herein by reference in their entireties. to their respective dihydrochalcones. Content of US 2013/0136839 (NUTRINOVA ) is a com FIELD OF THE INVENTION position of sweetening substances , including a sweetener 15 and at least one taste masking substance. Among the pos The invention is in the field of biotechnology and relates sible and various taste masking substances which can be to a method in which flavanone glycosides are converted used , naringin dihydrochalcone is found . without chemical intermediate steps to the corresponding EP 2529633 A1 ( SYMRISE ) finally describes an oral dihydrochalcones and to a corresponding microorganism , a edible composition , which can comprise among others nar vector and a host cell . 20 ingin dihydrochalcone and /or neohesperidin dihydrochal cone . PRIOR ART The object of the present invention was therefore to provide a method by means of which flavanone glycosides As part of a research program of the US Department of can be converted quickly and in high yields by biotechno Agriculture to reduce the bitter taste in citrus juices , in the 25 logical methods to the corresponding dihydrochalcones , mid 1960s a number of flavanone glycosides such as nar wherein chemical intermediate steps should be avoided ingin , hesperidin and narirutin were recognised as the crucial completely. bitter substances . Furthermore, it was found that the hydro genation of the flavanone glycosides to dihydrochalcones BRIEF DESCRIPTION OF THE DRAWINGS leads to substances that taste up to 1800 times sweeter than 30 sugar at the detection limit of the sweetening effect; if sugar FIG . 1 is a depicition of Plasmid pET28 CHI ALid . is exchanged for these dihydrochalcones in a weight ratio of FIG . 2 illustrates the SDS -PAGE of the expression of the 1 : 1 , the dihydrochalcones still prove to be more efficient by double transformation of pET22 ERED and pET28 CHI at least a factor of 300. Naringin dihydrochalcone, hesperi ALid , wherein Oh denotes the time point of the induction . din dihydrochalcone and neohesperidin dihydrochalcone are 35 FIG . 3 shows the conversion of naringin by means of currently not only among the most powerful sweeteners , but whole -cell - catalysis . are also useful in particular to mask the bitter taste of citrus substances . DESCRIPTION OF THE INVENTION Certain dihydrochalcone glycosides can be obtained by extraction from berries , especially from Malus spp . How- 40 A first subject matter of the invention relates to a process ever , the process is complicated , expensive and also depends for the preparation of flavanone glycoside dihydrochalcones on the season , and is therefore technically unimportant. comprising the steps of: Starting from flavanone glycosides the production of ( a ) provision of a transgenic microorganism containing dihydrochalcones is nowadays performed by catalytic ( i ) a first nucleic acid section ( A ) containing a gene coding reduction under strongly basic conditions or by a Friedel- 45 for a bacterial chalcone isomerase, and Crafts type acylation of phenols with dihydrocinnamic ( li ) a second nucleic acid section ( B ) containing a gene acids. Even though the synthesis is carried out in satisfactory coding for a bacterial enoate reductase gene yields and is industrially established , it has one major wherein the nucleic acid section ( A ) disadvantage however: it is a chemical manufacturing pro ( 1 ) represents a nucleotide sequence according to SEQ ID cess, which means that for regulatory reasons the final 50 NO : 1 , in which the nucleic acid section ( A ') according product cannot be declared natural. to SEQ ID NO : 3 has been cut out, or In this context, it is referred to the following documents ( 2 ) codes for an amino acid sequence according to SEQ in prior art : ID NO : 2 , in which the amino acid section ( A ') accord EP 2692729 A1 (SYMRISE ) discloses a process for ing to SEQ ID NO : 4 has been cut out, producing a dihydrochalcone using a transgenic microor- 55 (b ) addition of one or more flavanone glycosides to the ganism , comprising the following steps: Providing a trans transgenic microorganism , genic microorganism containing a nucleic acid section ( a ) ( c ) culturing the transgenic microorganism under conditions comprising or consisting of a gene coding for a bacterial which allow the simultaneous isomerisation and reduction chalcone isomerase , and /or a nucleic acid section ( a ') , com of the flavanone glycoside to the flavanone glycoside prising or consisting of a gene coding for a plant
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