Potassium Chloride → HCID 10557857, compound

HRID 590631Notes

Reaction equation

HRID 590631 reaction equation
CCC(CCCCC(N[C@H](C([NH:18][C@H:19]([C:23]([NH:25][C@H:26]([C:30]([NH:32][C@@H:33]1[C:61](=[O:62])[NH:60][C@H:59]([CH2:63][CH2:64][NH2:65])[C:57](=[O:58])[NH:56][C@H:55]([CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[C:53](=[O:54])[NH:52][C@@H:51]([CH2:73][CH:74]([CH3:76])[CH3:75])[C:49](=[O:50])[NH:48][C@@H:47]([CH2:77][CH2:78][NH2:79])[C:45](=[O:46])[NH:44][C@@H:43]([CH2:80][CH2:81][NH2:82])[C:41](=[O:42])[NH:40][C@@H:39]([C@H:83]([OH:85])[CH3:84])[C:37](=[O:38])[NH:36][CH2:35][CH2:34]1)=[O:31])[CH2:27][CH2:28][NH2:29])=[O:24])[C@H:20]([OH:22])[CH3:21])=O)CCN)=O)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[K+].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.N[C@H](C(O)=O)CS>CO>[CH3:84][C@@H:83]([OH:85])[C@@H:39]1[NH:40][C:41](=[O:42])[C@H:43]([CH2:80][CH2:81][NH2:82])[NH:44][C:45](=[O:46])[C@H:47]([CH2:77][CH2:78][NH2:79])[NH:48][C:49](=[O:50])[C@H:51]([CH2:73][CH:74]([CH3:75])[CH3:76])[NH:52][C:53](=[O:54])[C@H:55]([CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[NH:56][C:57](=[O:58])[C@H:59]([CH2:63][CH2:64][NH2:65])[NH:60][C:61](=[O:62])[C@@H:33]([NH:32][C:30]([C@@H:26]([NH:25][C:23]([C@@H:19]([NH2:18])[C@H:20]([OH:22])[CH3:21])=[O:24])[CH2:27][CH2:28][NH2:29])=[O:31])[CH2:34][CH2:35][NH:36][C:37]1=[O:38]

Participants

7

Reactant 5

HCID 4873Potassium ChlorideHCID 5862L-(+)-CysteineHCID 6049Ethylenediaminetetraacetic AcidHCID 62657Potassium Phosphate, TribasicHCID 498000041404-26-8

Product 1

HCID 10557857HCID 10557857, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Polymyxin B (20 g), immobilised papain (185 ELU/g), potassium phosphate buffer (25 mM; pH 7, 1.25 L), potassium chloride (30 mM), EDTA (10 mM) and cysteine (1 mM) was incubated at 37° C. for 18 h with gentle agitation. The progress of the reaction was monitored by LC-MS using the conditions outlined in Table 1. The immobilized papain was removed by filtration and the filtrate was concentrated in vacuo to leave a solid residue which was re-suspended in 10% aqueous methanol and left at room temperature overnight. The supernatant was decanted and concentrated in vacuo. Polymyxin B nonapeptide was purified from the residue by SPE on C18 silica, eluting with 0-10% aqueous methanol. Evaporation of the appropriate fractions gave the product as a white solid. m/z 482, [M+2H]2+

Workup

  1. customThe immobilized papain was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto leave a solid residue which
  4. waitleft at room temperature overnight
  5. customThe supernatant was decanted
  6. concentrationconcentrated in vacuo
  7. customPolymyxin B nonapeptide was purified from the residue by SPE on C18 silica
  8. washeluting with 0-10% aqueous methanol
  9. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-757d9ddc32d34083a73127f9a680b4c9
Source dataset
uspto-grants-2016_01
Patent number
US09234006B2

Reaction notes

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