Hydrochloric Acid → 5-Bromo-L-tryptophan

HRID 916271Notes

Reaction equation

HRID 916271 reaction equation
COC1C=C(CNCCCNCCCCNCCCN)C=CC=1O.[Br:25][NH:26][C@H:27]([C:38]([OH:40])=[O:39])[CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1.COC1C=C(CNCCCNCCCCNCCCNCC2C=CC(O)=C(OC)C=2)C=CC=1O.[Br:75][NH:76][C@H:77]([C:88]([OH:90])=[O:89])[CH2:78][C:79]1[C:87]2[C:82](=[CH:83][CH:84]=[CH:85][CH:86]=2)[NH:81][CH:80]=1.C1(N=C=S)C=CC=CC=1.Cl>CO.C(N(CC)CC)C.C(O)C>[Br:75][C:35]1[CH:36]=[C:37]2[C:32]([NH:31][CH:30]=[C:29]2[CH2:28][C@@H:27]([C:38]([OH:40])=[O:39])[NH2:26])=[CH:33][CH:34]=1.[Br:25][C:84]1[CH:83]=[C:82]2[C:87](=[CH:86][CH:85]=1)[C:79]([CH2:78][C@@H:77]([C:88]([OH:90])=[O:89])[NH2:76])=[CH:80][NH:81]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7673Phenyl IsothiocyanateHCID 131726598HCID 131726598, compoundHCID 131726599HCID 131726599, compound

Product 2

HCID 6443295-Bromo-L-tryptophanHCID 98569966-Bromo-L-tryptophan

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

To 200 nmols of DL-5-bromotryptophan or DL-6-bromotryptophan, 20 μl of ethanol:triethylamine:DW:phenyl isothiocyanate (sigma)=7:1:1:1 was added. The mixture was reacted at room temperature for 20 minutes. After drying, 50 μl of TFA was added thereto. The mixture was reacted at 50° C. for 10 minutes. After during, 50 μl of HCl: methanol=1:1 was added thereto, followed by reacting at 50° C. for 10 minutes. The reaction mixture was purified on reverse phase HPLC to give the PTH derivative of 5-bromotryptophan or 6-bromotryptophan. The final product was identified on a protein sequencer (FIGS. 17 and 18). These PTH derivatives were mixed with 20 amino acid PTH standard (ABI), and a protocol was prepared to separate the derivatives (TABLES 1 and 2). When the endogenous bovine GPR7 ligand was analyzed, the amino acid at the 1-position coincided with the peak of PTH-6-bromotryptophan (FIG. 19).

Workup

  1. customThe mixture was reacted at room temperature for 20 minutes
  2. customAfter drying
  3. addition50 μl of TFA was added
  4. customThe mixture was reacted at 50° C. for 10 minutes
  5. customThe reaction mixture was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-af8fa979735d4072a8992c19c8e49354
Source dataset
uspto-grants-2007_09
Patent number
US07268212B2

Reaction notes

Loading…