Claims
- 1. A method for converting a pradimicin compound of the following formula I or a salt thereof: to at least one pradimicin compound of the following formula II or salt thereof: ##STR14## where R.sup.1a is a disaccharide moiety selected from the group consisting of xylosyl-fucosyl, arabinosyl-fucosyl and fucosyl-fucosyl; or a monosaccharide moiety selected from the group consisting of fucosyl, 4-deoxyfucosyl and 4-deoxy-4-fluorofucosyl;
- when R.sup.1a is a disaccharide moiety, R.sup.1b is hydroxyl or a monosaccharide moiety, where said monosaccharide moiety contains the monosaccharide group of the R.sup.1a disaccharide moiety directly bonded to the aglycone; or, when R.sup.1a is a monosaccharide moiety, R.sup.1b is hydroxyl; and
- R.sup.2 is hydrogen, alkyl, hydroxyalkyl or arylalkyl;
- comprising the steps of contacting said pradimicin compound of the formula I or salt thereof with an enzyme or microorganism capable of catalyzing the hydrolysis of said compound I or salt thereof to form said compound II or salt thereof, and effecting said hydrolysis.
- 2. The method of claim 1, wherein
- R.sup.1a is fucosyl or xylosyl-fucosyl;
- R.sup.1b is hydroxyl or fucosyl; and
- R.sup.2 is methyl or hydroxymethyl.
- 3. The method of claim 2, wherein the compound having the following structure, or a salt thereof: ##STR15## is employed, and at least one of the compounds having the following structures, or salts thereof, are prepared: ##STR16##
- 4. The method of claim 2, wherein the compound having the following structure, or a salt thereof: is employed, and at least one of the compounds having the following structures, or salts thereof, are prepared: ##STR17##
- 5. The method of claim 1, wherein a microorganism is employed which belongs to one of the following genera: Actinomadura, Flavobacterium, Acinetobacter, Moraxella, Bacillus, Sporolactobacillus, Clostridium, Desulfotomaculum, Sporosarcina, Oscillospira, Planococcus, Lactobacillus, Kurthia, Micrococcus, Stomatococcus, Staphylococcus, Arthrobacter, Neisseria or Kingella, or wherein an enzyme derived from a microorganism belonging to one of said genera is employed.
- 6. The method of claim 5, wherein a microorganism is employed which belongs to the genus Flavobacterium, Moraxella, Micrococcus or Bacillus, or wherein an enzyme derived from a microorganism belonging to one of said genera is employed.
- 7. The method of claim 3, wherein a microorganism is employed which belongs to the genus Flavobacterium, Moraxella, Micrococcus or Bacillus, or wherein an enzyme derived from a microorganism belonging to one of said genera is employed.
- 8. The method of claim 6, wherein said microorganism, or the microorganism from which said enzyme is derived, is Moraxella sp. ATCC 55475.
- 9. A method for converting a pradimicin compound of the following formula II or a salt thereof: to at least one pradimicin compound of the following formula I or salt thereof: ##STR18## where R.sup.1b is hydroxyl or a monosacharide moiety which is fucosyl;
- when R.sup.1b is hydroxyl, R.sup.1a is a disaccharide moiety selected from the group consisting of xylosyl-fucosyl, arabinosyl-fucosyl and fucosyl-fucosyl, or a monosaccharide moiety selected from the group consisting of fucosyl, 4-deoxyfucosyl and 4-deoxy-4-fluorofucosyl; or, when R.sup.1b is a monosaccharide moiety, R.sup.1a is a disaccharide moiety selected from the group consisting of xylosyl-fucosyl, arabinosyl-fucosyl and fucosyl-fucosyl; and
- R.sup.2 is hydrogen, alkyl, hydroxyalkyl or arylalkyl;
- comprising the steps of contacting said pradimicin compound of the formula II or salt thereof with a sugar which is a monosaccharide selected from the group consisting of (i) fucose, 4-deoxyfucose and 4-deoxy-4-fluorofucose when R.sup.1b is hydroxyl, or (ii) xylose, arabinose and fucose when R.sup.1b is fucosyl; or a disaccharide selected from the group consisting of xylosyl-fucose, arabinosyl-fucose and fucosyl-fucose when R.sup.1b is hydroxyl; or with a glycoside of said sugar, and with an enzyme or microorganism capable of catalyzing the glycosidation of said compound II or salt thereof to form said compound I or salt thereof, with the proviso that said microorganism is not Actinomadura when R.sup.2 is methyl, and effecting said glycosidation.
- 10. The method of claim 9, wherein
- R.sup.1a is fucosyl or xylosyl-fucosyl;
- R.sup.1b is hydroxyl or fucosyl; and
- R.sup.2 is methyl or hydroxymethyl.
- 11. The method of claim 10, wherein the compound BMY-28960 having the following structure: ##STR19## or a salt thereof, is prepared.
- 12. The method of claim 9, wherein a microorganism is employed which belongs to one of the following genera: Actinomadura, Flavobacterium, Acinetobacter, Moraxella, Bacillus, Sporolactobacillus, Clostridium, Desulfotomaculum, Sporosarcina, Oscillospira, Planococcus, Lactobacillus, Kurthia, Micrococcus, Stomatococcus, Staphylococcus, Arthrobacter, Neisseria or Kingella, or wherein an enzyme derived from a microorganism belonging to one of said genera is employed.
- 13. The method of claim 12, wherein a microorganism is employed which belongs to the genus Flavobacterium, Moraxella, Micrococcus or Bacillus, or wherein an enzyme derived from a microorganism belonging to one of said genera is employed.
- 14. The method of claim 11, wherein a microorganism is employed which belongs to the genus Flavobacterium, Moraxella, Micrococcus or Bacillus, or wherein an enzyme derived from a microorganism belonging to one of said genera is employed.
- 15. The method of claim 13, wherein said microorganism, or the microorganism from which said enzyme is derived, is Moraxella sp. ATCC 55475.
Parent Case Info
This application is based on provisional U.S. application Ser. No. 60/006,158, filed Nov. 2, 1995.