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Information on EC 2.4.1.278 - 3-alpha-mycarosylerythronolide B desosaminyl transferase for references in articles please use BRENDA:EC2.4.1.278
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EC Tree
The enzyme appears in viruses and cellular organisms
Synonyms
DesVII, EryCIII, glycosyltransferase EryCIII,
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glycosyltransferase EryCIII
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dTDP-D-desosamine + 3-alpha-L-mycarosylerythronolide B = dTDP + erythromycin D
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dTDP-3-dimethylamino-3,4,6-trideoxy-alpha-D-glucopyranose:3-alpha-mycarosylerythronolide B 3-dimethylamino-3,4,6-trideoxy-beta-D-glucosyltransferase
The enzyme is involved in erythromycin biosynthesis.
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dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + 3-alpha-mycarosylerythronolide B
dTDP + erythromycin D
dTDP-D-desosamine + 3-alpha-L-mycarosylerythronolide B
dTDP + erythromycin D
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dTDP-D-mycaminose + 3-alpha-mycarosylerythronolide B
dTDP + erythromycin M
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the activated enzyme is capable of transferring an alternative sugar donor
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additional information
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no activity with: TDP-D-mycaminose, 6-deoxy-erythronolide B, 10-deoxymethynolide
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dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + 3-alpha-mycarosylerythronolide B
dTDP + erythromycin D
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dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose i.e. dTDP-D-desosamine
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dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + 3-alpha-mycarosylerythronolide B
dTDP + erythromycin D
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TDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose i.e. TDP-D-desosamine
product detected by HPLC. Identity is conformed via mass spectrometry and chromatographic comparison with an authentic reference standard
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dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + 3-alpha-mycarosylerythronolide B
dTDP + erythromycin D
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dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose i.e. dTDP-D-desosamine
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AKnT protein
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the noncognate glycosyltransferase activator protein AknT, stably activates EryCIII. Addition of purified AknT to inactive EryCIII restores the activity of EryCIII in vitro
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EryCII protein
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glycosyltransferase activator protein EryCII activates EryCIII. EryCIII treated with EryCII is catalytically active, effecting transfer of desosamine to 3-alpha-mycarosylerythronolide. The untreated EryCIII sample shows no activity
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0.05
3-alpha-mycarosylerythronolide B
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pH and temperature not specified in the publication, 0.05 mM dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
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0.017 - 1.7
3-alpha-mycarosylerythronolide B
1.7
dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
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pH 8.0, 25°C, in the presence og 0.001 mM EryC and 1 mM of each substrate, more than 300 turnovers are observed in 2.5 min, indicating that the kcat must be greater than 100/min. This is one of the highest turnover numbers reported for an antibiotic glycosyl transferase
0.017
3-alpha-mycarosylerythronolide B
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pH and temperature not specified in the publication, 0.05 mM TDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
1.7
3-alpha-mycarosylerythronolide B
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pH 8.0, 25°C, in the presence og 0.001 mM EryC and 1 mM of each substrate, more than 300 turnovers are observed in 2.5 min, indicating that the kcat must be greater than 100/min. This is one of the highest turnover numbers reported for an antibiotic glycosyl transferase
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0.34
3-alpha-mycarosylerythronolide B
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pH and temperature not specified in the publication, 0.05 mM dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose
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brenda
enzyme catalyzes reaction of EC 2.4.1.277
UniProt
brenda
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physiological function
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the enzyme is involved in erythromycin biosynthesis
physiological function
coexpression of glycosyltransferase DesVII and its auxiliary partner DesVIII in a Saccharopolyspora erythraea EryBV deletion mutant leads to an increased erythromycin A yield by 15% in comparison to Saccharopolyspora erythraea wild-type. DesVII/DesVIII replaced EryCIII to upload D-desosamine to C5 position of 3-O-mycarosyl erythronolide B and also in vivo attache L-mycarose, not D-desosamine to C3 position of erythronolide B with a higher activity than EryBV. Expression of DesVII in EryCIII and EryBV-CIII mutant strains partially restores the erythromycin A production, however, no erythromycin A is detected while DesVII is expressed in the EryBV mutant strain
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ERYC3_SACEN
Saccharopolyspora erythraea (strain ATCC 11635 / DSM 40517 / JCM 4748 / NBRC 13426 / NCIMB 8594 / NRRL 2338)
421
0
45929
Swiss-Prot
A0A3N6D581_9ACTN
285
0
30023
TrEMBL
A0A2K8PB61_STRLA
408
0
42513
TrEMBL
A0A1V2RLU2_9ACTN
410
0
43018
TrEMBL
A0A1D2I8U8_9ACTN
458
0
50931
TrEMBL
A0A178X5J8_9PSEU
420
0
46682
TrEMBL
A0A3N6GMS4_9ACTN
385
0
41151
TrEMBL
A0A1D8G1Z3_9ACTN
383
0
39905
TrEMBL
A0A4R8SX58_9MYCO
426
0
46168
TrEMBL
A0A221W4X9_9PSEU
420
0
45891
TrEMBL
A0A2P9FFJ9_9ACTN
413
0
45509
TrEMBL
A0A2P9F7W0_9ACTN
385
0
41104
TrEMBL
A0A405PDR6_9ZZZZ
95
0
10400
TrEMBL
A0A0M6Z0M7_9RHOB
426
0
46078
TrEMBL
A0ACI7_STRA7
Streptomyces ambofaciens (strain ATCC 23877 / 3486 / DSM 40053 / JCM 4204 / NBRC 12836 / NRRL B-2516)
418
0
45961
TrEMBL
A0A3N6CMP9_9ACTN
425
0
46833
TrEMBL
A0A0F6UB28_PSEAI
426
0
47059
TrEMBL
A0A2P4UPS6_9ACTN
395
0
41177
TrEMBL
A0A4R8SPE1_9MYCO
427
0
45827
TrEMBL
A0A4R8RW90_9MYCO
410
0
43246
TrEMBL
A0A1Q2Z5U4_9ACTN
424
0
45804
TrEMBL
A0A399GJP8_9ACTN
435
0
47719
TrEMBL
A0A1G4FN50_9FIRM
417
0
46564
TrEMBL
A0A1V5PJR5_9CHLR
162
1
17568
TrEMBL
W0S0M8_ECOLX
374
0
40882
TrEMBL
A0A161XHZ8_9RHOB
432
0
46647
TrEMBL
A0A3R3J508_9ZZZZ
95
0
10424
TrEMBL
A0A2K8QY02_9ACTN
417
0
46403
TrEMBL
A0A1Y2NMP3_STRFR
383
0
39919
TrEMBL
A0A3R3YN76_9ZZZZ
142
0
16015
TrEMBL
A0A221W1S1_9PSEU
389
0
40687
TrEMBL
A0A1Q2Z5Z8_9ACTN
425
0
46041
TrEMBL
A0A100JHD4_9ACTN
425
0
46026
TrEMBL
A0A406EDJ7_9ZZZZ
157
0
16274
TrEMBL
A0A1B2GN42_STRNR
424
0
46757
TrEMBL
A0A0C1LEN1_9PSEU
428
0
46539
TrEMBL
A0A3G4VN78_9ACTN
269
0
28287
TrEMBL
A0A1L7F9Q8_9PSEU
422
0
46060
TrEMBL
A0A3E2YFL4_9ACTN
416
0
44842
TrEMBL
A0A3R2K3X8_9ZZZZ
162
0
17159
TrEMBL
A0A221W4R6_9PSEU
428
0
46711
TrEMBL
A0A1V2RA68_9ACTN
427
0
46140
TrEMBL
A0A3E2YFM3_9ACTN
443
0
48346
TrEMBL
A0A2Z5JSW1_9ACTN
409
0
42883
TrEMBL
A0A445NFY7_STRNE
397
0
42606
TrEMBL
A0A177HIY6_9ACTN
439
0
48256
TrEMBL
A0A0D1EHM4_9RHOB
451
0
47926
TrEMBL
A0A1J5S9C2_9ZZZZ
418
0
45865
TrEMBL
A0A1V2RFX0_9ACTN
442
0
47010
TrEMBL
A0A3E2YTA7_9ACTN
420
0
44446
TrEMBL
A0A405NNJ4_9ZZZZ
96
0
10461
TrEMBL
A0A405PE68_9ZZZZ
92
0
9880
TrEMBL
A0A2Z5K6N5_9ACTN
426
0
46764
TrEMBL
A0A178WRS9_9PSEU
384
0
40878
TrEMBL
A0A080LZL3_9PROT
405
0
45131
TrEMBL
A0A4R8QZR1_9MYCO
426
0
45266
TrEMBL
A0A1V2RBP7_9ACTN
444
0
47729
TrEMBL
A0A3E2YHB6_9ACTN
424
0
46592
TrEMBL
A0A3R1GMB0_9ZZZZ
398
0
43648
TrEMBL
A0A3R4YIV1_9ZZZZ
95
0
10391
TrEMBL
A0A3R4YMR8_9ZZZZ
157
0
16308
TrEMBL
A0A2Z5K6P3_9ACTN
430
0
47620
TrEMBL
A0A0M6ZVM9_9RHOB
430
0
46704
TrEMBL
A0A405NKU3_9ZZZZ
90
0
9912
TrEMBL
A0A3R4IW60_9ZZZZ
133
0
14096
TrEMBL
A0A2Z5K6Q1_9ACTN
439
0
47740
TrEMBL
A0A445NGC3_STRNE
418
0
43794
TrEMBL
A0A178X5I7_9PSEU
298
0
30539
TrEMBL
A0A178WQ02_9PSEU
415
0
46308
TrEMBL
Q8GH22_ECOLX
371
0
40278
TrEMBL
A0A4P6Q723_9ACTN
422
0
46428
TrEMBL
A0A0M7AMH7_9RHOB
435
0
46927
TrEMBL
A0A100J0X7_9ACTN
424
0
45791
TrEMBL
DES7_STRVZ
426
0
46423
Swiss-Prot
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4°C, activity of concentrated enzyme stored overnight is more than 3 times lower than that of freshly purified enzyme.
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coexpression of EryCIII with the GroEL/ES chaperone complex greatly enhances the expression of soluble EryCIII protein
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expression in Escherichia coli BL21(DE3) as a C-terminal His6 fusion protein
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medicine
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potential use to make unnatural macrolides for use as antibacterial
medicine
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the activated enzyme is capable of transferring an alternative unnatural sugar donor. Because the desosamine sugar contacts the 50S subunit of ribosome, the discovery that an unnatural sugar can be transferred has implications for the synthesis of new erythromycin derivatives with improved properties. Reconstitute of the activity of EryCIII in vitro for the synthesis of unnatural macrolides
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Lee, H.Y.; Chung, H.S.; Hang, C.; Khosla, C.; Walsh, C.T.; Kahne, D.; Walker, S.
Reconstitution and characterization of a new desosaminyl transferase, EryCIII, from the erythromycin biosynthetic pathway
J. Am. Chem. Soc.
126
9924-9925
2004
Saccharopolyspora erythraea
brenda
Yuan, Y.; Chung, H.S.; Leimkuhler, C.; Walsh, C.T.; Kahne, D.; Walker, S.
In vitro reconstitution of EryCIII activity for the preparation of unnatural macrolides
J. Am. Chem. Soc.
127
14128-14129
2005
Saccharopolyspora erythraea
brenda
Wu, H.; Li, W.; Xin, C.; Zhang, C.; Wang, Y.; Ren, S.; Ren, M.; Zhao, W.; Yuan, L.; Xu, Z.; Yuan, H.; Geng, M.; Zhang, L.; Weaver, D.T.; Zhang, B.
In vivo investigation to the macrolide-glycosylating enzyme pair DesVII/DesVIII in Saccharopolyspora erythraea
Appl. Microbiol. Biotechnol.
100
2257-2266
2016
Streptomyces venezuelae (Q9ZGH7)
brenda
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2.4.1.278 3-alpha-mycarosylerythronolide B desosaminyl transferase
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