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Literature summary extracted from

  • Rose, T.M.; Prestwich, G.D.
    Synthesis and evaluation of fluorogenic substrates for phospholipase D and phospholipase C (2006), Org. Lett., 8, 2575-2578.
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
3.1.4.3 analysis synthesis of fluorogenic analogue of phosphatidylcholine 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine, and use as direct substrate for real-time measurement of enzyme activity. Substrate for both phospholipases C and D and lysophospholipase D, no substrate for Bacillus cereus PI-PLC or Clostridium perfringens PC-PLC Bacillus cereus
3.1.4.4 analysis synthesis of fluorogenic analogue of phosphatidylcholine 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine, and use as direct substrate for real-time measurement of enzyme activity. 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine is substrate for both phospholipases C and D Saccharomyces cerevisiae
3.1.4.4 analysis synthesis of fluorogenic analogue of phosphatidylcholine 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine, and use as direct substrate for real-time measurement of enzyme activity. 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine is substrate for both phospholipases C and D Arachis hypogaea
3.1.4.4 analysis synthesis of fluorogenic analogue of phosphatidylcholine 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine, and use as direct substrate for real-time measurement of enzyme activity. 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine is substrate for both phospholipases C and D Streptomyces sp.
3.1.4.4 analysis synthesis of fluorogenic analogue of phosphatidylcholine 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine, and use as direct substrate for real-time measurement of enzyme activity. 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine is substrate for both phospholipases C and D Brassica oleracea
3.1.4.39 analysis fluorogenic substrates, potential in screening for inhibitors and for monitoring spatiotemporal changes in activity in cells Bacillus cereus
3.1.4.39 analysis fluorogenic substrates, potential in screening for inhibitors and for monitoring spatiotemporal changes in activity in cells Clostridium perfringens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.1.4.39 lysophosphatidylcholine + H2O Bacillus cereus
-
 lysophosphatidic acid + choline
-
 ?
3.1.4.39 lysophosphatidylcholine + H2O Clostridium perfringens
-
 lysophosphatidic acid + choline
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.1.4.3 Bacillus cereus
-
 isoform PC-PLC
-
3.1.4.4 Arachis hypogaea
-
 commercial preparation
-
3.1.4.4 Brassica oleracea
-
 commercial preparation
-
3.1.4.4 Saccharomyces cerevisiae
-
-
-
3.1.4.4 Streptomyces sp.
-
 commercial preparation
-
3.1.4.39 Bacillus cereus
-
-
-
3.1.4.39 Clostridium perfringens
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.4.3 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine + H2O fluorogenic analogue of phosphatidylcholine, direct substrate for real-time measurement of enzyme activity Bacillus cereus ?
-
 ?
3.1.4.4 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine + H2O fluorogenic analogue of phosphatidylcholine, direct substrate for real-time measurement of enzyme activity Saccharomyces cerevisiae ?
-
 ?
3.1.4.4 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine + H2O fluorogenic analogue of phosphatidylcholine, direct substrate for real-time measurement of enzyme activity Arachis hypogaea ?
-
 ?
3.1.4.4 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine + H2O fluorogenic analogue of phosphatidylcholine, direct substrate for real-time measurement of enzyme activity Streptomyces sp. ?
-
 ?
3.1.4.4 1-O-(6-(p-methyl red)-amino-hexanoyl)-2-O-(12-(p-methyl red)-amino-dodecanoyl)-sn-glyceryl-N-(3-(5-BODIPY-pentanoyl)-amino-propyl)-N,Ndimethyl-phosphatidylethanolamine + H2O fluorogenic analogue of phosphatidylcholine, direct substrate for real-time measurement of enzyme activity Brassica oleracea ?
-
 ?
3.1.4.39 lysoDDPB + H2O synthesized by an enzyme-assisted strategy. Lysophosphatidylcholine analogue that contains a fluorescence quencher at each acyl chain terminus and a fluorophore appended to the phospholipid headgroup through a choline-mimetic linker Bacillus cereus ?
-
 ?
3.1.4.39 lysophosphatidylcholine + H2O
-
 Bacillus cereus lysophosphatidic acid + choline
-
 ?
3.1.4.39 lysophosphatidylcholine + H2O
-
 Clostridium perfringens lysophosphatidic acid + choline
-
 ?
3.1.4.39 [(11R)-1-(4-[(Z)-[4-(dimethylamino)phenyl]diazenyl]phenyl)-N-[3-[(5-[5-[(3,5-dimethyl-2H-pyrrol-2-ylidene-kappaN)methyl]-1H-pyrrol-2-yl-kappaN]pentanoyl)amino]propyl]-11,14-dihydroxy-N,N-dimethyl-1,8-dioxo-9,13,15-trioxa-2-aza-14-phosphaheptadecan-17-aminiumato 14-oxide](difluoro)boron(1+) + H2O synthesized by an enzyme-assisted strategy. lysophosphatidylcholine analogue that contains a fluorescence quencher at each acyl chain terminus and a fluorophore append to the phospholipid headgroup through a choline-mimetic linker Clostridium perfringens ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.1.4.39 lysophospholipase D
-
 Bacillus cereus
3.1.4.39 lysophospholipase D
-
 Clostridium perfringens
3.1.4.39 lysoPLD
-
 Bacillus cereus
3.1.4.39 lysoPLD
-
 Clostridium perfringens
3.1.4.39 lysoPLD autotaxin nucleotide pyrophosphatase/phosphodiesterase, catalyzes hydrolysis via an active site threonine Bacillus cereus
3.1.4.39 lysoPLD autotaxin nucleotide pyrophosphatase/phosphodiesterase, catalyzes hydrolysis via an active site threonine Clostridium perfringens