                         SEQUENCE LISTING

<110>  SERTURNER CORP.
 
<120>  N-ALKYLATION OF ALKALOID COMPOUNDS

<130>  21806-P53700PC00

<150>  US 62/538,918
<151>  2017-07-31

<160>  7     

<170>  PatentIn version 3.5

<210>  1
<211>  1119
<212>  DNA
<213>  Ephedra sinica

<400>  1
atgagaggat cgcatcacca tcaccatcac ggatccatgg aagaagcaaa aatggcgacc       60

ctgggcggtg cgtcctatgc gatgattgtg aaaacgatga tgcgctctct ggaagcaaac      120

ctgattccgg attttgtgct gcgtcgcctg acgcgtatcc tgctggctag tcgcctgaaa      180

ctgggttata agcagaccgc tgaactgcaa ctggcggatc tgatgtcatt cgttgcgtcg      240

ctgaaaacga tgccgattgc cctgtgcacc gaagaagcaa agggtcagca ttacgaactg      300

ccgaccagct ttttcaaact ggtcctgggc aaacatctga agtatagctc tgcctacttt      360

tctgaacaca cccgtacgct ggatgaagcg gaagaagcca tgctggcact gtattgcgaa      420

cgcgccaaaa ttgaagatgg tcagaagatt ctggacatcg gctgtggttg gggcagtttt      480

tccctgtatg tggcagaacg ttacccgaaa tgcgaaatta cgggcctgtg taacagttcc      540

acccaaaaag ccttcatcga acagcaatgc agcgaacgtc gcctgtgtaa tgttaccatt      600

tatgcagatg acatcagcac ctttgatacg gaatctacct acgaccgcat tatcagcatc      660

gaaatgttcg aacacatgaa gaactacagt acgctgctga agaaaattag caagtggatg      720

aatcaggaat gcctgctgtt tgtccattat ttctgtcaca aaacctttgc gtaccacttc      780

gaagatgtgg acgaagatga ctggatggct cgttatttct ttaccggcgg caccatgccg      840

gcgtcatcgc tgctgctgta ctttcaggat gacgtctcag tggttgatca ttggctgatt      900

aacggtaaac actatgctca aacctcggaa gaatggctga agcgtatgga ccacaatctg      960

agctctattc tgccgatctt taacgaaacg tatggcgaaa atgcggccaa aaagtggctg     1020

gcatactggc gcaccttttt catcgcagtt gctgaactgt tcaaatacaa cgatggcgaa     1080

gaatggatgg tgtcccactt cctgttcaaa aagaaataa                            1119


<210>  2
<211>  372
<212>  PRT
<213>  Ephedra sinica

<400>  2

Met Arg Gly Ser His His His His His His Gly Ser Met Glu Glu Ala 
1               5                   10                  15      


Lys Met Ala Thr Leu Gly Gly Ala Ser Tyr Ala Met Ile Val Lys Thr 
            20                  25                  30          


Met Met Arg Ser Leu Glu Ala Asn Leu Ile Pro Asp Phe Val Leu Arg 
        35                  40                  45              


Arg Leu Thr Arg Ile Leu Leu Ala Ser Arg Leu Lys Leu Gly Tyr Lys 
    50                  55                  60                  


Gln Thr Ala Glu Leu Gln Leu Ala Asp Leu Met Ser Phe Val Ala Ser 
65                  70                  75                  80  


Leu Lys Thr Met Pro Ile Ala Leu Cys Thr Glu Glu Ala Lys Gly Gln 
                85                  90                  95      


His Tyr Glu Leu Pro Thr Ser Phe Phe Lys Leu Val Leu Gly Lys His 
            100                 105                 110         


Leu Lys Tyr Ser Ser Ala Tyr Phe Ser Glu His Thr Arg Thr Leu Asp 
        115                 120                 125             


Glu Ala Glu Glu Ala Met Leu Ala Leu Tyr Cys Glu Arg Ala Lys Ile 
    130                 135                 140                 


Glu Asp Gly Gln Lys Ile Leu Asp Ile Gly Cys Gly Trp Gly Ser Phe 
145                 150                 155                 160 


Ser Leu Tyr Val Ala Glu Arg Tyr Pro Lys Cys Glu Ile Thr Gly Leu 
                165                 170                 175     


Cys Asn Ser Ser Thr Gln Lys Ala Phe Ile Glu Gln Gln Cys Ser Glu 
            180                 185                 190         


Arg Arg Leu Cys Asn Val Thr Ile Tyr Ala Asp Asp Ile Ser Thr Phe 
        195                 200                 205             


Asp Thr Glu Ser Thr Tyr Asp Arg Ile Ile Ser Ile Glu Met Phe Glu 
    210                 215                 220                 


His Met Lys Asn Tyr Ser Thr Leu Leu Lys Lys Ile Ser Lys Trp Met 
225                 230                 235                 240 


Asn Gln Glu Cys Leu Leu Phe Val His Tyr Phe Cys His Lys Thr Phe 
                245                 250                 255     


Ala Tyr His Phe Glu Asp Val Asp Glu Asp Asp Trp Met Ala Arg Tyr 
            260                 265                 270         


Phe Phe Thr Gly Gly Thr Met Pro Ala Ser Ser Leu Leu Leu Tyr Phe 
        275                 280                 285             


Gln Asp Asp Val Ser Val Val Asp His Trp Leu Ile Asn Gly Lys His 
    290                 295                 300                 


Tyr Ala Gln Thr Ser Glu Glu Trp Leu Lys Arg Met Asp His Asn Leu 
305                 310                 315                 320 


Ser Ser Ile Leu Pro Ile Phe Asn Glu Thr Tyr Gly Glu Asn Ala Ala 
                325                 330                 335     


Lys Lys Trp Leu Ala Tyr Trp Arg Thr Phe Phe Ile Ala Val Ala Glu 
            340                 345                 350         


Leu Phe Lys Tyr Asn Asp Gly Glu Glu Trp Met Val Ser His Phe Leu 
        355                 360                 365             


Phe Lys Lys Lys 
    370         


<210>  3
<211>  388
<212>  PRT
<213>  Glaucium flavum

<400>  3

Met Gly Ser Ser His His His His His His Gly Thr Gly Ser Tyr Ile 
1               5                   10                  15      


Thr Ser Leu Tyr Lys Lys Ala Gly Trp Asp Leu Met Ala Thr Ser Lys 
            20                  25                  30          


Gln Val Lys Lys Lys Glu Glu Leu Leu Lys Asn Met Glu Leu Gly Leu 
        35                  40                  45              


Val Pro Asp Glu Glu Ile Arg Arg Leu Ile Arg Ile Glu Leu Glu Lys 
    50                  55                  60                  


Arg Leu Lys Trp Gly Tyr Lys Pro Thr His Gln Gln Gln Leu Ala Gln 
65                  70                  75                  80  


Leu Leu Asp Leu Val His Ser Leu Lys Lys Met Lys Ile Ala Thr Glu 
                85                  90                  95      


Met Glu Ser Leu Asp Leu Lys Leu Tyr Glu Ala Pro Phe Ser Phe Val 
            100                 105                 110         


Gln Ile Lys His Gly Ser Thr Ile Lys Glu Ser Ser Ser Tyr Phe Lys 
        115                 120                 125             


Asp Glu Ser Met Thr Leu Asp Glu Ala Glu Ile Ala Met Leu Asp Leu 
    130                 135                 140                 


Tyr Val Glu Arg Ala Gln Ile Glu Asp Gly Gln Ser Val Leu Asp Leu 
145                 150                 155                 160 


Gly Cys Gly Leu Gly Ala Val Thr Leu His Val Ala Lys Lys Tyr Lys 
                165                 170                 175     


Asn Cys His Val Thr Gly Leu Thr Asn Ser Val Glu Gln Lys Asp Phe 
            180                 185                 190         


Ile Glu Gly Lys Cys Lys Glu Leu Asn Leu Ser Asn Val Lys Val Ile 
        195                 200                 205             


Leu Ala Asp Val Thr Ser His Glu Met Glu Asp Lys Phe Asp Arg Ile 
    210                 215                 220                 


Phe Ala Val Glu Leu Ile Glu His Met Lys Asn Tyr Glu Leu Leu Leu 
225                 230                 235                 240 


Arg Arg Ile Ser Lys Trp Met Lys Asp Asp Gly Leu Leu Phe Ile Glu 
                245                 250                 255     


His Val Cys His Lys Thr Phe Ala Tyr His Tyr Glu Pro Ile Asp Glu 
            260                 265                 270         


Asp Asp Trp Tyr Thr Glu Tyr Ile Phe Pro Ala Gly Thr Leu Thr Leu 
        275                 280                 285             


Ser Ser Ala Ser Leu Leu Leu Tyr Phe Gln Asp Asp Val Ser Val Val 
    290                 295                 300                 


Asn His Trp Thr Leu Ser Gly Lys His Tyr Ser Arg Ser His Glu Glu 
305                 310                 315                 320 


Trp Leu Lys Arg Ile Asp Gly Asn Met Asp Ala Val Lys Glu Ile Met 
                325                 330                 335     


Lys Ser Ile Thr Lys Thr Glu Glu Glu Ala Val Lys Leu Ile Asn Phe 
            340                 345                 350         


Trp Arg Ile Phe Cys Met Cys Gly Ala Glu Leu Phe Gly Tyr Lys Asp 
        355                 360                 365             


Gly Glu Glu Trp Met Met Ser His Val Leu Phe Lys Lys Lys Gln Leu 
    370                 375                 380                 


Leu Gln Gln Cys 
385             


<210>  4
<211>  382
<212>  PRT
<213>  Glaucium flavum

<400>  4

Met Gly Ser Ser His His His His His His Gly Thr Gly Ser Tyr Ile 
1               5                   10                  15      


Thr Ser Leu Tyr Lys Lys Ala Gly Trp Gly Ser Asn Glu Ala Gln Val 
            20                  25                  30          


Lys Lys Glu Ser Ile Gly Glu Ile Met Gly Lys Leu Met Gln Gly Glu 
        35                  40                  45              


Ile Gly Asp Glu Glu Leu Ser Lys Arg Ile Lys Glu Ile Phe Gly Lys 
    50                  55                  60                  


Arg Leu Gln Trp Gly Tyr Lys Pro Thr His Gln Gln Gln Leu Ala Phe 
65                  70                  75                  80  


Asn Leu Asp Phe Ile Lys Ser Leu Lys Glu Met Asp Met Ser Gly Glu 
                85                  90                  95      


Ile Asp Thr Met Asn Glu Glu Thr Tyr Glu Leu Pro Ser Ala Phe Leu 
            100                 105                 110         


Glu Ala Ala Phe Gly Lys Thr Ile Lys Gln Ser Gly Cys Tyr Phe Lys 
        115                 120                 125             


Asp Glu Thr Thr Thr Ile Asp Glu Ala Glu Glu Ala Ser His Glu Leu 
    130                 135                 140                 


Tyr Cys Glu Arg Ala Gln Ile Lys Asp Gly Gln Thr Val Leu Asp Ile 
145                 150                 155                 160 


Gly Cys Gly Gln Gly Gly Leu Val Leu His Ile Ala Gln Lys Tyr Lys 
                165                 170                 175     


Asn Cys His Val Thr Gly Leu Thr Asn Ser Lys Ala Gln Lys Asn Tyr 
            180                 185                 190         


Ile Leu Met Gln Ala Glu Lys Leu Gln Leu Ser Asn Val Asp Val Ile 
        195                 200                 205             


Leu Ala Asp Val Thr Lys His Glu Ser Asp Lys Thr Tyr Asp Arg Ile 
    210                 215                 220                 


Leu Val Ile Glu Thr Ile Glu His Met Lys Asn Ile Gln Leu Phe Met 
225                 230                 235                 240 


Lys Lys Leu Ser Thr Trp Met Thr Glu Asp Ser Leu Leu Phe Val Asp 
                245                 250                 255     


His Ile Cys His Lys Thr Phe Ser His His Phe Glu Ala Ile Asp Glu 
            260                 265                 270         


Asp Asp Trp Tyr Ser Gly Phe Ile Phe Pro Lys Gly Cys Val Thr Ile 
        275                 280                 285             


Leu Ser Ala Ser Ala Leu Leu Tyr Phe Gln Asp Asp Val Thr Ile Leu 
    290                 295                 300                 


Asp His Trp Val Val Asn Gly Met His Met Ala Arg Ser Val Asp Ala 
305                 310                 315                 320 


Trp Arg Lys Lys Leu Asp Lys Asn Met Glu Leu Ala Arg Glu Ile Leu 
                325                 330                 335     


Leu Pro Gly Leu Gly Ser Lys Glu Ala Val Asn Gly Val Ile Thr His 
            340                 345                 350         


Ile Arg Thr Phe Cys Met Gly Gly Tyr Glu Gln Phe Ser Tyr Asn Asn 
        355                 360                 365             


Gly Glu Glu Trp Met Val Ala Gln Met Leu Phe Lys Lys Lys 
    370                 375                 380         


<210>  5
<211>  387
<212>  PRT
<213>  Papaver somniferum

<400>  5

Met Gly Ser Ser His His His His His His Gly Thr Gly Ser Tyr Ile 
1               5                   10                  15      


Thr Ser Leu Tyr Lys Lys Ala Gly Trp Ser Thr Thr Met Glu Thr Thr 
            20                  25                  30          


Lys Ile Ser Gln Gln Asp Asp Leu Trp Lys Asn Met Glu Leu Gly Gln 
        35                  40                  45              


Ile Ser Asp Glu Glu Val Arg Arg Leu Met Lys Ile Gly Ile Glu Lys 
    50                  55                  60                  


Arg Ile Lys Trp Gly Thr Lys Pro Thr Gln Gln Glu Gln Leu Ala Gln 
65                  70                  75                  80  


Leu Leu Asp Phe Asn Lys Ser Leu Arg Gly Met Lys Met Ala Thr Glu 
                85                  90                  95      


Ile Asp Thr Leu Glu Asn His Lys Ile Tyr Glu Thr Pro Glu Ser Phe 
            100                 105                 110         


Asn Gln Ile Ile Gly Gly Lys Glu Ser Ala Gly Leu Phe Thr Asp Glu 
        115                 120                 125             


Thr Thr Thr Thr Met Glu Glu Ala Asn Thr Lys Met Met Asp Leu Tyr 
    130                 135                 140                 


Cys Glu Arg Ala Gly Leu Lys Asp Gly His Thr Ile Leu Asp Leu Gly 
145                 150                 155                 160 


Cys Gly Ala Gly Leu Leu Val Leu His Leu Ala Lys Lys Tyr Lys Lys 
                165                 170                 175     


Ser Lys Ile Thr Gly Ile Thr Asn Thr Ser Ser His Lys Glu Tyr Ile 
            180                 185                 190         


Leu Lys Gln Cys Lys Asn Leu Asn Leu Ser Asn Val Glu Ile Ile Leu 
        195                 200                 205             


Ala Asp Val Thr Lys Val Asp Ile Glu Ser Thr Phe Asp Arg Val Phe 
    210                 215                 220                 


Val Ile Gly Leu Ile Glu His Met Lys Asn Phe Glu Leu Phe Leu Arg 
225                 230                 235                 240 


Lys Ile Ser Lys Trp Met Lys Asp Asp Gly Leu Leu Leu Leu Glu His 
                245                 250                 255     


Leu Cys His Lys Ser Phe Ser Asp His Trp Glu Pro Leu Ser Glu Asp 
            260                 265                 270         


Asp Trp Tyr Ala Lys Asn Phe Phe Pro Ser Gly Thr Leu Val Ile Pro 
        275                 280                 285             


Ser Ala Thr Cys Leu Leu Tyr Phe Gln Glu Asp Val Thr Val Ile Asp 
    290                 295                 300                 


His Trp Ile Leu Ser Gly Asn Asn Phe Ala Arg Ser Asn Glu Val Ile 
305                 310                 315                 320 


Leu Lys Arg Ile Asp Gly Lys Ile Glu Glu Val Lys Asp Ile Phe Met 
                325                 330                 335     


Ser Phe Tyr Gly Ile Gly Arg Glu Glu Ala Val Lys Leu Ile Asn Trp 
            340                 345                 350         


Trp Arg Leu Leu Cys Ile Thr Ala Asn Glu Leu Phe Lys Tyr Asn Asn 
        355                 360                 365             


Gly Glu Glu Trp Leu Ile Ser Gln Leu Leu Phe Lys Lys Lys Leu Met 
    370                 375                 380                 


Thr Cys Ile 
385         


<210>  6
<211>  1083
<212>  DNA
<213>  Native Ephedra sinica

<400>  6
atggaagagg cgaagatggc aacgctgggc ggtgcctcgt atgccatgat agtgaagaca       60

atgatgcgct ctctcgaagc caacctaatt ccggacttcg tactgagaag gctcactcgc      120

attctcttgg cgagtcgtct gaagctcgga tacaagcaaa ccgcggagct tcagcttgct      180

gatctcatgt cctttgttgc atcgttaaag accatgccta tagctctctg caccgaagaa      240

gctaaaggcc agcattacga gctgcccact tcgttcttca agttggttct cggcaagcat      300

ctcaaataca gctcggctta cttcagtgaa cacacaagaa ctctagatga agcagaggaa      360

gcaatgttag cactgtattg tgagagggct aagattgaag atggccaaaa gattctggat      420

ataggatgtg gatggggttc attttcttta tatgttgctg aaagataccc aaaatgtgaa      480

ataactggtc tttgcaattc ctctacccag aaggcgttta tagagcaaca gtgcagtgaa      540

agaagacttt gcaatgttac tatatatgct gatgatatta gcacttttga tacggagagt      600

acttatgatc gcataatatc tattgaaatg tttgagcaca tgaaaaatta cagtactctt      660

cttaaaaaaa tatcaaagtg gatgaatcag gaatgcttgc tgtttgtgca ttatttttgt      720

cataagacat ttgcttacca ttttgaggat gtagatgaag atgattggat ggcaagatac      780

tttttcacag gtggcacaat gcctgcaagt agcttactac tgtattttca ggatgatgtt      840

tcagttgttg atcactggct tataaatggg aagcactatg ctcaaacaag tgaagagtgg      900

ctgaaaagga tggaccataa tctatcctct atacttccta tatttaatga aacatatggc      960

gaaaatgcag ctaaaaagtg gttggcatac tggcgaacat tctttattgc cgtggctgag     1020

ctttttaagt acaatgatgg agaagaatgg atggtttcac attttctgtt taagaaaaaa     1080

tag                                                                   1083


<210>  7
<211>  360
<212>  PRT
<213>  Native Ephedra sinica

<400>  7

Met Glu Glu Ala Lys Met Ala Thr Leu Gly Gly Ala Ser Tyr Ala Met 
1               5                   10                  15      


Ile Val Lys Thr Met Met Arg Ser Leu Glu Ala Asn Leu Ile Pro Asp 
            20                  25                  30          


Phe Val Leu Arg Arg Leu Thr Arg Ile Leu Leu Ala Ser Arg Leu Lys 
        35                  40                  45              


Leu Gly Tyr Lys Gln Thr Ala Glu Leu Gln Leu Ala Asp Leu Met Ser 
    50                  55                  60                  


Phe Val Ala Ser Leu Lys Thr Met Pro Ile Ala Leu Cys Thr Glu Glu 
65                  70                  75                  80  


Ala Lys Gly Gln His Tyr Glu Leu Pro Thr Ser Phe Phe Lys Leu Val 
                85                  90                  95      


Leu Gly Lys His Leu Lys Tyr Ser Ser Ala Tyr Phe Ser Glu His Thr 
            100                 105                 110         


Arg Thr Leu Asp Glu Ala Glu Glu Ala Met Leu Ala Leu Tyr Cys Glu 
        115                 120                 125             


Arg Ala Lys Ile Glu Asp Gly Gln Lys Ile Leu Asp Ile Gly Cys Gly 
    130                 135                 140                 


Trp Gly Ser Phe Ser Leu Tyr Val Ala Glu Arg Tyr Pro Lys Cys Glu 
145                 150                 155                 160 


Ile Thr Gly Leu Cys Asn Ser Ser Thr Gln Lys Ala Phe Ile Glu Gln 
                165                 170                 175     


Gln Cys Ser Glu Arg Arg Leu Cys Asn Val Thr Ile Tyr Ala Asp Asp 
            180                 185                 190         


Ile Ser Thr Phe Asp Thr Glu Ser Thr Tyr Asp Arg Ile Ile Ser Ile 
        195                 200                 205             


Glu Met Phe Glu His Met Lys Asn Tyr Ser Thr Leu Leu Lys Lys Ile 
    210                 215                 220                 


Ser Lys Trp Met Asn Gln Glu Cys Leu Leu Phe Val His Tyr Phe Cys 
225                 230                 235                 240 


His Lys Thr Phe Ala Tyr His Phe Glu Asp Val Asp Glu Asp Asp Trp 
                245                 250                 255     


Met Ala Arg Tyr Phe Phe Thr Gly Gly Thr Met Pro Ala Ser Ser Leu 
            260                 265                 270         


Leu Leu Tyr Phe Gln Asp Asp Val Ser Val Val Asp His Trp Leu Ile 
        275                 280                 285             


Asn Gly Lys His Tyr Ala Gln Thr Ser Glu Glu Trp Leu Lys Arg Met 
    290                 295                 300                 


Asp His Asn Leu Ser Ser Ile Leu Pro Ile Phe Asn Glu Thr Tyr Gly 
305                 310                 315                 320 


Glu Asn Ala Ala Lys Lys Trp Leu Ala Tyr Trp Arg Thr Phe Phe Ile 
                325                 330                 335     


Ala Val Ala Glu Leu Phe Lys Tyr Asn Asp Gly Glu Glu Trp Met Val 
            340                 345                 350         


Ser His Phe Leu Phe Lys Lys Lys 
        355                 360 


