                         SEQUENCE LISTING

<110>  Emergent Product Development Gaithersburg Inc.
 
<120>  DEOXYNOJIRIMYCIN DERIVATIVES AS GLUCOSIDASE INHIBITORS

<130>  EPDG.14194PRV

<160>  3     

<170>  PatentIn version 3.5

<210>  1
<211>  843
<212>  PRT
<213>  Synthetic

<400>  1

Met Ala Arg Gly Glu Arg Arg Arg Arg Ala Val Pro Ala Glu Gly Val 
1               5                   10                  15      


Arg Thr Ala Glu Arg Ala Ala Arg Gly Gly Pro Gly Arg Arg Asp Gly 
            20                  25                  30          


Arg Gly Gly Gly Pro Arg Ser Thr Ala Gly Gly Val Ala Leu Ala Val 
        35                  40                  45              


Val Val Leu Ser Leu Ala Leu Gly Met Ser Gly Arg Trp Val Leu Ala 
    50                  55                  60                  


Trp Tyr Arg Ala Arg Arg Ala Val Thr Leu His Ser Ala Pro Pro Val 
65                  70                  75                  80  


Leu Pro Ala Asp Ser Ser Ser Pro Ala Val Ala Pro Asp Leu Phe Trp 
                85                  90                  95      


Gly Thr Tyr Arg Pro His Val Tyr Phe Gly Met Lys Thr Arg Ser Pro 
            100                 105                 110         


Lys Pro Leu Leu Thr Gly Leu Met Trp Ala Gln Gln Gly Thr Thr Pro 
        115                 120                 125             


Gly Thr Pro Lys Leu Arg His Thr Cys Glu Gln Gly Asp Gly Val Gly 
    130                 135                 140                 


Pro Tyr Gly Trp Glu Phe His Asp Gly Leu Ser Phe Gly Arg Gln His 
145                 150                 155                 160 


Ile Gln Asp Gly Ala Leu Arg Leu Thr Thr Glu Phe Val Lys Arg Pro 
                165                 170                 175     


Gly Gly Gln His Gly Gly Asp Trp Ser Trp Arg Val Thr Val Glu Pro 
            180                 185                 190         


Gln Asp Ser Gly Thr Ser Ala Leu Pro Leu Val Ser Leu Phe Phe Tyr 
        195                 200                 205             


Val Val Thr Asp Gly Lys Glu Val Leu Leu Pro Glu Val Gly Ala Lys 
    210                 215                 220                 


Gly Gln Leu Lys Phe Ile Ser Gly His Thr Ser Glu Leu Gly Asp Phe 
225                 230                 235                 240 


Arg Phe Thr Leu Leu Pro Pro Thr Ser Pro Gly Asp Thr Ala Pro Lys 
                245                 250                 255     


Tyr Gly Ser Tyr Asn Val Phe Trp Thr Ser Asn Pro Gly Leu Pro Leu 
            260                 265                 270         


Leu Thr Glu Met Val Lys Ser Arg Leu Asn Ser Trp Phe Gln His Arg 
        275                 280                 285             


Pro Pro Gly Ala Pro Pro Glu Arg Tyr Leu Gly Leu Pro Gly Ser Leu 
    290                 295                 300                 


Lys Trp Glu Asp Arg Gly Pro Ser Gly Gln Gly Gln Gly Gln Phe Leu 
305                 310                 315                 320 


Ile Gln Gln Val Thr Leu Lys Ile Pro Ile Ser Ile Glu Phe Val Phe 
                325                 330                 335     


Glu Ser Gly Ser Ala Gln Ala Gly Gly Asn Gln Ala Leu Pro Arg Leu 
            340                 345                 350         


Ala Gly Ser Leu Leu Thr Gln Ala Leu Glu Ser His Ala Glu Gly Phe 
        355                 360                 365             


Arg Glu Arg Phe Glu Lys Thr Phe Gln Leu Lys Glu Lys Gly Leu Ser 
    370                 375                 380                 


Ser Gly Glu Gln Val Leu Gly Gln Ala Ala Leu Ser Gly Leu Leu Gly 
385                 390                 395                 400 


Gly Ile Gly Tyr Phe Tyr Gly Gln Gly Leu Val Leu Pro Asp Ile Gly 
                405                 410                 415     


Val Glu Gly Ser Glu Gln Lys Val Asp Pro Ala Leu Phe Pro Pro Val 
            420                 425                 430         


Pro Leu Phe Thr Ala Val Pro Ser Arg Ser Phe Phe Pro Arg Gly Phe 
        435                 440                 445             


Leu Trp Asp Glu Gly Phe His Gln Leu Val Val Gln Arg Trp Asp Pro 
    450                 455                 460                 


Ser Leu Thr Arg Glu Ala Leu Gly His Trp Leu Gly Leu Leu Asn Ala 
465                 470                 475                 480 


Asp Gly Trp Ile Gly Arg Glu Gln Ile Leu Gly Asp Glu Ala Arg Ala 
                485                 490                 495     


Arg Val Pro Pro Glu Phe Leu Val Gln Arg Ala Val His Ala Asn Pro 
            500                 505                 510         


Pro Thr Leu Leu Leu Pro Val Ala His Met Leu Glu Val Gly Asp Pro 
        515                 520                 525             


Asp Asp Leu Ala Phe Leu Arg Lys Ala Leu Pro Arg Leu His Ala Trp 
    530                 535                 540                 


Phe Ser Trp Leu His Gln Ser Gln Ala Gly Pro Leu Pro Leu Ser Tyr 
545                 550                 555                 560 


Arg Trp Arg Gly Arg Asp Pro Ala Leu Pro Thr Leu Leu Asn Pro Lys 
                565                 570                 575     


Thr Leu Pro Ser Gly Leu Asp Asp Tyr Pro Arg Ala Ser His Pro Ser 
            580                 585                 590         


Val Thr Glu Arg His Leu Asp Leu Arg Cys Trp Val Ala Leu Gly Ala 
        595                 600                 605             


Arg Val Leu Thr Arg Leu Ala Glu His Leu Gly Glu Ala Glu Val Ala 
    610                 615                 620                 


Ala Glu Leu Gly Pro Leu Ala Ala Ser Leu Glu Ala Ala Glu Ser Leu 
625                 630                 635                 640 


Asp Glu Leu His Trp Ala Pro Glu Leu Gly Val Phe Ala Asp Phe Gly 
                645                 650                 655     


Asn His Thr Lys Ala Val Gln Leu Lys Pro Arg Pro Pro Gln Gly Leu 
            660                 665                 670         


Val Arg Val Val Gly Arg Pro Gln Pro Gln Leu Gln Tyr Val Asp Ala 
        675                 680                 685             


Leu Gly Tyr Val Ser Leu Phe Pro Leu Leu Leu Arg Leu Leu Asp Pro 
    690                 695                 700                 


Thr Ser Ser Arg Leu Gly Pro Leu Leu Asp Ile Leu Ala Asp Ser Arg 
705                 710                 715                 720 


His Leu Trp Ser Pro Phe Gly Leu Arg Ser Leu Ala Ala Ser Ser Ser 
                725                 730                 735     


Phe Tyr Gly Gln Arg Asn Ser Glu His Asp Pro Pro Tyr Trp Arg Gly 
            740                 745                 750         


Ala Val Trp Leu Asn Val Asn Tyr Leu Ala Leu Gly Ala Leu His His 
        755                 760                 765             


Tyr Gly His Leu Glu Gly Pro His Gln Ala Arg Ala Ala Lys Leu His 
    770                 775                 780                 


Gly Glu Leu Arg Ala Asn Val Val Gly Asn Val Trp Arg Gln Tyr Gln 
785                 790                 795                 800 


Ala Thr Gly Phe Leu Trp Glu Gln Tyr Ser Asp Arg Asp Gly Arg Gly 
                805                 810                 815     


Met Gly Cys Arg Pro Phe His Gly Trp Thr Ser Leu Val Leu Leu Ala 
            820                 825                 830         


Met Ala Glu Asp Tyr His His His His His His 
        835                 840             


<210>  2
<211>  976
<212>  PRT
<213>  Synthetic

<400>  2

Met Gly Ile Leu Pro Ser Pro Gly Met Pro Ala Leu Leu Ser Leu Val 
1               5                   10                  15      


Ser Leu Leu Ser Val Leu Leu Met Gly Cys Val Ala Glu Thr Gly Ala 
            20                  25                  30          


Val Asp Arg Ser Asn Phe Lys Thr Cys Asp Glu Ser Ser Phe Cys Lys 
        35                  40                  45              


Arg Gln Arg Ser Ile Arg Pro Gly Leu Ser Pro Tyr Arg Ala Leu Leu 
    50                  55                  60                  


Asp Thr Leu Gln Leu Gly Pro Asp Ala Leu Thr Val His Leu Ile His 
65                  70                  75                  80  


Glu Val Thr Lys Val Leu Leu Val Leu Glu Leu Gln Gly Leu Gln Lys 
                85                  90                  95      


Asn Met Thr Arg Ile Arg Ile Asp Glu Leu Glu Pro Arg Arg Pro Arg 
            100                 105                 110         


Tyr Arg Val Pro Asp Val Leu Val Ala Asp Pro Pro Thr Ala Arg Leu 
        115                 120                 125             


Ser Val Ser Gly Arg Asp Asp Asn Ser Val Glu Leu Thr Val Ala Glu 
    130                 135                 140                 


Gly Pro Tyr Lys Ile Ile Leu Thr Ala Gln Pro Phe Arg Leu Asp Leu 
145                 150                 155                 160 


Leu Glu Asp Arg Ser Leu Leu Leu Ser Val Asn Ala Arg Gly Leu Met 
                165                 170                 175     


Ala Phe Glu His Gln Arg Ala Pro Arg Val Pro Phe Ser Asp Lys Val 
            180                 185                 190         


Ser Leu Ala Leu Gly Ser Val Trp Asp Lys Ile Lys Asn Leu Phe Ser 
        195                 200                 205             


Arg Gln Glu Ser Lys Asp Pro Ala Glu Gly Asn Gly Ala Gln Pro Glu 
    210                 215                 220                 


Ala Thr Pro Gly Asp Gly Asp Lys Pro Glu Glu Thr Gln Glu Lys Ala 
225                 230                 235                 240 


Glu Lys Asp Glu Pro Gly Ala Trp Glu Glu Thr Phe Lys Thr His Ser 
                245                 250                 255     


Asp Ser Lys Pro Tyr Gly Pro Thr Ser Val Gly Leu Asp Phe Ser Leu 
            260                 265                 270         


Pro Gly Met Glu His Val Tyr Gly Ile Pro Glu His Ala Asp Ser Leu 
        275                 280                 285             


Arg Leu Lys Val Thr Glu Gly Gly Glu Pro Tyr Arg Leu Tyr Asn Leu 
    290                 295                 300                 


Asp Val Phe Gln Tyr Glu Leu Asn Asn Pro Met Ala Leu Tyr Gly Ser 
305                 310                 315                 320 


Val Pro Val Leu Leu Ala His Ser Phe His Arg Asp Leu Gly Ile Phe 
                325                 330                 335     


Trp Leu Asn Ala Ala Glu Thr Trp Val Asp Ile Ser Ser Asn Thr Ala 
            340                 345                 350         


Gly Lys Thr Leu Phe Gly Lys Met Leu Asp Tyr Leu Gln Gly Ser Gly 
        355                 360                 365             


Glu Thr Pro Gln Thr Asp Ile Arg Trp Met Ser Glu Ser Gly Ile Ile 
    370                 375                 380                 


Asp Val Phe Leu Met Leu Gly Pro Ser Val Phe Asp Val Phe Arg Gln 
385                 390                 395                 400 


Tyr Ala Ser Leu Thr Gly Thr Gln Ala Leu Pro Pro Leu Phe Ser Leu 
                405                 410                 415     


Gly Tyr His Gln Ser Arg Trp Asn Tyr Arg Asp Glu Ala Asp Val Leu 
            420                 425                 430         


Glu Val Asp Gln Gly Phe Asp Asp His Asn Met Pro Cys Asp Val Ile 
        435                 440                 445             


Trp Leu Asp Ile Glu His Ala Asp Gly Lys Arg Tyr Phe Thr Trp Asp 
    450                 455                 460                 


Pro Thr Arg Phe Pro Gln Pro Leu Asn Met Leu Glu His Leu Ala Ser 
465                 470                 475                 480 


Lys Arg Arg Lys Leu Val Ala Ile Val Asp Pro His Ile Lys Val Asp 
                485                 490                 495     


Ser Gly Tyr Arg Val His Glu Glu Leu Arg Asn His Gly Leu Tyr Val 
            500                 505                 510         


Lys Thr Arg Asp Gly Ser Asp Tyr Glu Gly Trp Cys Trp Pro Gly Ser 
        515                 520                 525             


Ala Ser Tyr Pro Asp Phe Thr Asn Pro Arg Met Arg Ala Trp Trp Ser 
    530                 535                 540                 


Asn Met Phe Ser Phe Asp Asn Tyr Glu Gly Ser Ala Pro Asn Leu Tyr 
545                 550                 555                 560 


Val Trp Asn Asp Met Asn Glu Pro Ser Val Phe Asn Gly Pro Glu Val 
                565                 570                 575     


Thr Met Leu Lys Asp Ala Val His Tyr Gly Gly Trp Glu His Arg Asp 
            580                 585                 590         


Ile His Asn Ile Tyr Gly Leu Tyr Val His Met Ala Thr Ala Asp Gly 
        595                 600                 605             


Leu Ile Gln Arg Ser Gly Gly Ile Glu Arg Pro Phe Val Leu Ser Arg 
    610                 615                 620                 


Ala Phe Phe Ser Gly Ser Gln Arg Phe Gly Ala Val Trp Thr Gly Asp 
625                 630                 635                 640 


Asn Thr Ala Glu Trp Asp His Leu Lys Ile Ser Ile Pro Met Cys Leu 
                645                 650                 655     


Ser Leu Ala Leu Val Gly Leu Ser Phe Cys Gly Ala Asp Val Gly Gly 
            660                 665                 670         


Phe Phe Lys Asn Pro Glu Pro Glu Leu Leu Val Arg Trp Tyr Gln Met 
        675                 680                 685             


Gly Ala Tyr Gln Pro Phe Phe Arg Ala His Ala His Leu Asp Thr Gly 
    690                 695                 700                 


Arg Arg Glu Pro Trp Leu Leu Ala Ser Gln Tyr Gln Asp Ala Ile Arg 
705                 710                 715                 720 


Asp Ala Leu Phe Gln Arg Tyr Ser Leu Leu Pro Phe Trp Tyr Thr Leu 
                725                 730                 735     


Phe Tyr Gln Ala His Lys Glu Gly Phe Pro Val Met Arg Pro Leu Trp 
            740                 745                 750         


Val Gln Tyr Pro Glu Asp Met Ser Thr Phe Ser Ile Glu Asp Gln Phe 
        755                 760                 765             


Met Leu Gly Asp Ala Leu Leu Ile His Pro Val Ser Asp Ala Gly Ala 
    770                 775                 780                 


His Gly Val Gln Val Tyr Leu Pro Gly Gln Glu Glu Val Trp Tyr Asp 
785                 790                 795                 800 


Ile Gln Ser Tyr Gln Lys His His Gly Pro Gln Thr Leu Tyr Leu Pro 
                805                 810                 815     


Val Thr Leu Ser Ser Ile Pro Val Phe Gln Arg Gly Gly Thr Ile Val 
            820                 825                 830         


Pro Arg Trp Met Arg Val Arg Arg Ser Ser Asp Cys Met Lys Asp Asp 
        835                 840                 845             


Pro Ile Thr Leu Phe Val Ala Leu Ser Pro Gln Gly Thr Ala Gln Gly 
    850                 855                 860                 


Glu Leu Phe Leu Asp Asp Gly His Thr Phe Asn Tyr Gln Thr Arg His 
865                 870                 875                 880 


Glu Phe Leu Leu Arg Arg Phe Ser Phe Ser Gly Ser Thr Leu Val Ser 
                885                 890                 895     


Ser Ser Ala Asp Pro Lys Gly His Leu Glu Thr Pro Ile Trp Ile Glu 
            900                 905                 910         


Arg Val Val Ile Met Gly Ala Gly Lys Pro Ala Ala Val Val Leu Gln 
        915                 920                 925             


Thr Lys Gly Ser Pro Glu Ser Arg Leu Ser Phe Gln His Asp Pro Glu 
    930                 935                 940                 


Thr Ser Val Leu Ile Leu Arg Lys Pro Gly Val Ser Val Ala Ser Asp 
945                 950                 955                 960 


Trp Ser Ile His Leu Arg Ala Ser Trp Ser His Pro Gln Phe Glu Lys 
                965                 970                 975     


<210>  3
<211>  542
<212>  PRT
<213>  Synthetic

<400>  3

Met Gly Ile Leu Pro Ser Pro Gly Met Pro Ala Leu Leu Ser Leu Val 
1               5                   10                  15      


Ser Leu Leu Ser Val Leu Leu Met Gly Cys Val Ala Glu Thr Gly Ala 
            20                  25                  30          


Val Glu Val Lys Arg Pro Arg Gly Val Ser Leu Ser Asn His His Phe 
        35                  40                  45              


Tyr Glu Glu Ser Lys Pro Phe Thr Cys Leu Asp Gly Thr Ala Thr Ile 
    50                  55                  60                  


Pro Phe Asp Gln Val Asn Asp Asp Tyr Cys Asp Cys Lys Asp Gly Ser 
65                  70                  75                  80  


Asp Glu Pro Gly Thr Ala Ala Cys Pro Asn Gly Ser Phe His Cys Thr 
                85                  90                  95      


Asn Thr Gly Tyr Lys Pro Leu Tyr Ile Leu Ser Ser Arg Val Asn Asp 
            100                 105                 110         


Gly Val Cys Asp Cys Cys Asp Gly Thr Asp Glu Tyr Asn Ser Gly Thr 
        115                 120                 125             


Val Cys Glu Asn Thr Cys Arg Glu Lys Gly Arg Lys Glu Lys Glu Ser 
    130                 135                 140                 


Leu Gln Gln Leu Ala Glu Val Thr Arg Glu Gly Phe Arg Leu Lys Lys 
145                 150                 155                 160 


Ile Leu Ile Glu Glu Trp Lys Thr Ala Arg Glu Glu Lys Gln Ser Lys 
                165                 170                 175     


Leu Leu Glu Leu Gln Ala Gly Lys Lys Ser Leu Glu Asp Gln Val Glu 
            180                 185                 190         


Thr Leu Arg Ala Ala Lys Glu Glu Ala Glu Arg Pro Glu Lys Glu Ala 
        195                 200                 205             


Lys Asp Gln His Arg Lys Leu Trp Glu Glu Gln Gln Ala Ala Ala Lys 
    210                 215                 220                 


Ala Arg Arg Glu Gln Glu Arg Ala Ala Ser Ala Phe Gln Glu Leu Asp 
225                 230                 235                 240 


Asp Asn Met Asp Gly Met Val Ser Leu Ala Glu Leu Gln Thr His Pro 
                245                 250                 255     


Glu Leu Asp Thr Asp Gly Asp Gly Ala Leu Ser Glu Glu Glu Ala Gln 
            260                 265                 270         


Ala Leu Leu Ser Gly Asp Thr Gln Thr Asp Thr Thr Ser Phe Tyr Asp 
        275                 280                 285             


Arg Val Trp Ala Ala Ile Arg Asp Lys Tyr Arg Ser Glu Val Pro Pro 
    290                 295                 300                 


Thr Asp Ile Pro Val Pro Glu Glu Thr Glu Pro Lys Glu Glu Lys Pro 
305                 310                 315                 320 


Pro Val Leu Pro Pro Thr Glu Glu Glu Glu Glu Glu Glu Glu Glu Pro 
                325                 330                 335     


Glu Glu Glu Glu Glu Glu Glu Glu Glu Glu Glu Glu Ala Pro Pro Pro 
            340                 345                 350         


Leu Gln Pro Pro Gln Pro Pro Ser Pro Thr Glu Asp Glu Lys Met Pro 
        355                 360                 365             


Pro Tyr Asp Glu Glu Thr Gln Ala Ile Ile Asp Ala Ala Gln Glu Ala 
    370                 375                 380                 


Arg Ser Lys Phe Glu Glu Val Glu Arg Ser Leu Lys Glu Met Glu Glu 
385                 390                 395                 400 


Ser Ile Arg Ser Leu Glu Gln Glu Ile Ser Phe Asp Phe Gly Pro Ser 
                405                 410                 415     


Gly Glu Phe Ala Tyr Leu Tyr Ser Gln Cys Tyr Glu Leu Thr Thr Asn 
            420                 425                 430         


Glu Tyr Val Tyr Arg Leu Cys Pro Phe Lys Leu Val Ser Gln Lys Pro 
        435                 440                 445             


Lys His Gly Gly Ser Pro Thr Ser Leu Gly Thr Trp Gly Ser Trp Ala 
    450                 455                 460                 


Gly Pro Asp His Asp Lys Phe Ser Ala Met Lys Tyr Glu Gln Gly Thr 
465                 470                 475                 480 


Gly Cys Trp Gln Gly Pro Asn Arg Ser Thr Thr Val Arg Leu Leu Cys 
                485                 490                 495     


Gly Lys Glu Thr Val Val Thr Ser Thr Thr Glu Pro Ser Arg Cys Glu 
            500                 505                 510         


Tyr Leu Met Glu Leu Met Thr Pro Ala Ala Cys Pro Glu Pro Pro Pro 
        515                 520                 525             


Glu Ala Pro Ser Asp Gly Asp Lys His His His His His His 
    530                 535                 540         


