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Information on EC 2.4.1.278 - 3-alpha-mycarosylerythronolide B desosaminyl transferase
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2.4.1.278 3-alpha-mycarosylerythronolide B desosaminyl transferaseIUBMB Comments
The enzyme is involved in erythromycin biosynthesis.
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Word Map
- 2.4.1.278
- erythromycin
-
saccharopolyspora
-
macrolide
- erythraea
- polyketide
- glycosyltransferases
-
deoxysugars
-
d-desosamine
-
erythromycin-producing
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macrolactone
- peucetius
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6-deoxyerythronolide
- medicine
-
spinosyns
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interspecies
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14-membered
- antibioticus
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auxiliary
-
aglycone
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
DesVII, EryCIII, glycosyltransferase EryCIII, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dTDP-D-desosamine + 3-alpha-L-mycarosylerythronolide B = dTDP + erythromycin D
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-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
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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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
-
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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?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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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-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
-
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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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
-
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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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). ERYC3_SACEN
Saccharopolyspora erythraea (strain ATCC 11635 / DSM 40517 / JCM 4748 / NBRC 13426 / NCIMB 8594 / NRRL 2338)
421
0
45929
Swiss-Prot
-
A0A1Y2NMP3_STRFR
383
0
39919
TrEMBL
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A0A1J5S9C2_9ZZZZ
418
0
45865
TrEMBL
other Location (Reliability: 5)
A0ACI7_STRA7
Streptomyces ambofaciens (strain ATCC 23877 / 3486 / DSM 40053 / JCM 4204 / NBRC 12836 / NRRL B-2516)
418
0
45961
TrEMBL
-
A0A1V5PJR5_9CHLR
162
1
17568
TrEMBL
-
A0A080LZL3_9PROT
405
0
45131
TrEMBL
-
A0A4P7C5M0_9PSEU
430
0
45009
TrEMBL
Mitochondrion (Reliability: 5)
A0A2K8PB61_STRLA
408
0
42513
TrEMBL
-
A0A517NPK8_9BACT
387
0
43215
TrEMBL
-
A0A1B2GN42_STRNR
424
0
46757
TrEMBL
-
A0A6B9B9I1_MYCAV
396
0
43553
TrEMBL
-
A0A1B2GN19_STRNR
422
0
46312
TrEMBL
-
A0A6B9B850_MYCAV
388
0
41096
TrEMBL
-
A0A6B9BGM6_MYCAV
400
0
41862
TrEMBL
-
A0A1L7F9Q8_9PSEU
422
0
46060
TrEMBL
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, activity of concentrated enzyme stored overnight is more than 3 times lower than that of freshly purified enzyme.
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
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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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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)
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