Sulfurmycin A → HCID 101282619, compound

HRID 1065255Notes

Reaction equation

HRID 1065255 reaction equation
C[C@@H]1O[C@@H](O[C@@H]2C3C(O)=C4C(=O)C5C(O)=CC=CC=5C(=O)C4=CC=3[C@@H](C(OC)=O)[C@@](O)(C)C2)C[C@H](N(C)C)[C@@H]1O[C@@H]1O[C@@H](C)[C@@H](O[C@@H]2O[C@@H](C)C(=O)CC2)[C@@H](O)C1.C[C@@H]1O[C@@H](O[C@H]2[C@@H](N(C)C)C[C@H](O[C@@H]3C4C(O)=C5C(=O)C6C(O)=CC=CC=6C(=O)C5=CC=4[C@@H](C(OC)=O)[C@@](O)(C)C3)O[C@H]2C)C[C@@H]2O[C@@H]3[C@H](O[C@H]12)O[C@@H](C)C(=O)C3.C[C@@H]1O[C@@H](O[C@@H:123]2[C:128]3[C:129]([OH:144])=[C:130]4[C:137](=[O:138])[C:136]5[C:139]([OH:143])=[CH:140][CH:141]=[CH:142][C:135]=5[C:133](=[O:134])[C:131]4=[CH:132][C:127]=3[C@@H:126]([C:145]([O:147][CH3:148])=[O:146])[C@@:125]([OH:153])([CH2:149][C:150]([CH3:152])=[O:151])[CH2:124]2)C[C@H](N(C)C)[C@@H]1O[C@@H]1O[C@@H](C)[C@@H](O[C@@H]2O[C@@H](C)C(=O)CC2)[C@@H](O)C1.C[C@@H]1O[C@@H](O[C@H]2[C@@H](N(C)C)C[C@H](O[C@@H]3C4C(O)=C5C(=O)C6C(O)=CC=CC=6C(=O)C5=CC=4[C@@H](C(OC)=O)[C@@](O)(CC(C)=O)C3)O[C@H]2C)C[C@@H]2O[C@@H]3[C@H](O[C@H]12)O[C@@H](C)C(=O)C3>>[CH3:152][C:150]([CH2:149][C@:125]1([OH:153])[C@H:126]([C:145]([O:147][CH3:148])=[O:146])[C:127]2[CH:132]=[C:131]3[C:133](=[O:134])[C:135]4[CH:142]=[CH:141][CH:140]=[C:139]([OH:143])[C:136]=4[C:137](=[O:138])[C:130]3=[C:129]([OH:144])[C:128]=2[CH2:123][CH2:124]1)=[O:151]

Participants

5

Reactant 4

HCID 155836Sulfurmycin AHCID 155837Auramycin BHCID 155838Methyl 2,5,7-trihydroxy-2-methyl-6,11-dioxo-4-({2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-(6-methyl-5-oxooxan-2-yl)hexopyranosyl]-3-(dimethylamino)hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylateHCID 155839sulfurmycin B

Product 1

HCID 101282619HCID 101282619, compound

Procedure

A 500 ml Erlenmeyer flask with 100 ml of vegetative culture of Streptomyces galilaeus OBB-111, obtained by a process analogous to that described in Example 1, containing auramycin A, auramycin B, sulfurmycin A and sulfurmycin B, was allowed to stand at room temperature for 12 hours and extracted with 200 ml of a solvent mixture of chloroform and methanol (1:1, v/v). The chloroform layer was separated, concentrated in vacuo and chromatographed by thin layer chromatography (toluene/methanol=20:1, v/v). The bands containing 7-deoxysulfurmycinone and 7-deoxyauramycinone were scraped off, extracted with chloroform and concentrated in vacuo to dryness to give 1.4 mg of pure 7-deoxysulfurmycinone and 1.2 mg of pure 7-deoxyauramycinone, respectively.

Workup

  1. customA 500 ml Erlenmeyer flask with 100 ml of vegetative culture of Streptomyces galilaeus OBB-111, obtained by a process analogous to
  2. extractionextracted with 200 ml of a solvent mixture of chloroform and methanol (1:1
  3. customThe chloroform layer was separated
  4. concentrationconcentrated in vacuo
  5. customchromatographed by thin layer chromatography (toluene/methanol=20:1, v/v)
  6. additionThe bands containing 7-deoxysulfurmycinone and 7-deoxyauramycinone
  7. extractionextracted with chloroform
  8. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-ef63508474144543b688cdc271bc0769
Source dataset
uspto-grants-1982_05
Patent number
US04329339

Reaction notes

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