Dicyclohexylcarbodiimide → HCID 131723815, compound

HRID 1862178Notes

Reaction equation

HRID 1862178 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O.CN(C1C=CC=CN=1)C.[CH3:49][C@H:50]([NH:171][C:172]([CH2:174][NH:175][C:176]([C@@H:178]([NH:182][CH:183]=[O:184])[CH:179]([CH3:181])[CH3:180])=[O:177])=[O:173])[C:51]([NH:53][C@@H:54]([C:59]([NH:61][C@H:62]([C:64]([NH:66][C@@H:67]([C:71]([NH:73][C@H:74]([C:78]([NH:80][C@H:81]([C:85]([NH:87][C@H:88]([C:99]([NH:101][C@@H:102]([C:107]([NH:109][C@H:110]([C:121]([NH:123][C@@H:124]([C:129]([NH:131][C@H:132]([C:143]([NH:145][C@@H:146]([C:151]([NH:153][C@H:154]([C:165]([NH:167][CH2:168][CH2:169][OH:170])=[O:166])[CH2:155][C:156]1[C:164]2[C:159](=[CH:160][CH:161]=[CH:162][CH:163]=2)[NH:158][CH:157]=1)=[O:152])[CH2:147][CH:148]([CH3:150])[CH3:149])=[O:144])[CH2:133][C:134]1[C:142]2[C:137](=[CH:138][CH:139]=[CH:140][CH:141]=2)[NH:136][CH:135]=1)=[O:130])[CH2:125][CH:126]([CH3:128])[CH3:127])=[O:122])[CH2:111][C:112]1[C:120]2[C:115](=[CH:116][CH:117]=[CH:118][CH:119]=2)[NH:114][CH:113]=1)=[O:108])[CH2:103][CH:104]([CH3:106])[CH3:105])=[O:100])[CH2:89][C:90]1[C:98]2[C:93](=[CH:94][CH:95]=[CH:96][CH:97]=2)[NH:92][CH:91]=1)=[O:86])[CH:82]([CH3:84])[CH3:83])=[O:79])[CH:75]([CH3:77])[CH3:76])=[O:72])[CH:68]([CH3:70])[CH3:69])=[O:65])[CH3:63])=[O:60])[CH2:55][CH:56]([CH3:58])[CH3:57])=[O:52]>ClCCl.CO.C(N(CC)CC)C>[OH:3][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:1].[CH3:49][C@H:50]([NH:171][C:172]([CH2:174][NH:175][C:176]([C@@H:178]([NH:182][CH:183]=[O:184])[CH:179]([CH3:181])[CH3:180])=[O:177])=[O:173])[C:51]([NH:53][C@@H:54]([C:59]([NH:61][C@H:62]([C:64]([NH:66][C@@H:67]([C:71]([NH:73][C@H:74]([C:78]([NH:80][C@H:81]([C:85]([NH:87][C@H:88]([C:99]([NH:101][C@@H:102]([C:107]([NH:109][C@H:110]([C:121]([NH:123][C@@H:124]([C:129]([NH:131][C@H:132]([C:143]([NH:145][C@@H:146]([C:151]([NH:153][C@H:154]([C:165]([NH:167][CH2:168][CH2:169][OH:170])=[O:166])[CH2:155][C:156]1[C:164]2[C:159](=[CH:160][CH:161]=[CH:162][CH:163]=2)[NH:158][CH:157]=1)=[O:152])[CH2:147][CH:148]([CH3:149])[CH3:150])=[O:144])[CH2:133][C:134]1[C:142]2[C:137](=[CH:138][CH:139]=[CH:140][CH:141]=2)[NH:136][CH:135]=1)=[O:130])[CH2:125][CH:126]([CH3:127])[CH3:128])=[O:122])[CH2:111][C:112]1[C:120]2[C:115](=[CH:116][CH:117]=[CH:118][CH:119]=2)[NH:114][CH:113]=1)=[O:108])[CH2:103][CH:104]([CH3:105])[CH3:106])=[O:100])[CH2:89][C:90]1[C:98]2[C:93](=[CH:94][CH:95]=[CH:96][CH:97]=2)[NH:92][CH:91]=1)=[O:86])[CH:82]([CH3:83])[CH3:84])=[O:79])[CH:75]([CH3:76])[CH3:77])=[O:72])[CH:68]([CH3:69])[CH3:70])=[O:65])[CH3:63])=[O:60])[CH2:55][CH:56]([CH3:57])[CH3:58])=[O:52]

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 80170N-HydroxysuccinimideHCID 171548Biotin2×HCID 161301401405-97-62×

Product 1

HCID 131723815HCID 131723815, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A photo-generatable derivative of biotin (so called caged biotin) was prepared by a modification of the method of Pirrung et al (Bioconj. Chem., 1996, 7, 317). This compound (9 mg) was dissolved in dichloromethane (5 ml) and treated with dicyclohexylcarbodimide (DCC) (3 mg), N-hydroxy succinimide (NHS) (2 mg) and dimethylaminopyridine (0.2 mg). After stirring at room temperature for two hours a derivative of gramicidin bearing two aminocaproyl groups linked end-to-end and attached to the terminal hydroxyl of gramicidin (prepared by conventional peptide chemistry techniques) was added (30 mg, as a solution in methanol (1 ml) and triethylamine (0.1 ml)). The solution was stirred for 18 hours, evaporated to dryness and then passed through a Sephadex LH-20 column eluting with dichloromethane-methanol-water (800:50:4). The main fraction was then purified by HPLC on a 40 mm×200 mm Waters Prep Nova-Pak® HR silica column (6 μm, 6 Å) eluting with dichloromethane-methanol-water (800:40:4) operating at a flow rate of 25 ml/min. The fraction, eluting at 24.5 minutes, possessed a 1H-nmr spectrum and mass spectrum in full agreement with the proposed structure.

Workup

  1. additionwas added (30 mg
  2. customevaporated to dryness
  3. washcolumn eluting with dichloromethane-methanol-water (800:50:4)
  4. customThe main fraction was then purified by HPLC on a 40 mm×200 mm Waters Prep Nova-Pak® HR silica column (6 μm, 6 Å)
  5. washeluting with dichloromethane-methanol-water (800:40:4) operating at a flow rate of 25 ml/min
  6. washThe fraction, eluting at 24.5 minutes

Sources & evidence

ORD record
ord-813ebdd195fb49899867c67e3e094a37
Source dataset
uspto-grants-2003_03
Patent number
US06537441B1

Reaction notes

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