Hydrochloric Acid → 2-azido-L-tyrosine

HRID 1197681

반응식

HRID 1197681 반응식
[N:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)=[N+:2]=[N-:3].[C:11]([OH:16])(=[O:15])[C:12]([CH3:14])=O.CC1C(O)=C(C=O)C(COP(O)(O)=O)=C[N:19]=1.C([O-])(=O)C.[NH4+].C1(O)C=CC=CC=1.N[C@H](C(O)=O)CC1C=CC(O)=CC=1.[NH4+].[OH-].N(C1C=CC=CC=1O)=[N+]=[N-].Cl.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>O.C(O)(=O)C>[N:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][C:9]=1[CH2:14][C@@H:12]([C:11]([OH:16])=[O:15])[NH2:19])=[N+:2]=[N-:3]

참가 물질

12

반응물 9

HCID 313Hydrochloric AcidHCID 1051Pyridoxal 5'-phosphateHCID 1060Pyruvic AcidHCID 10236NinhydrinHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 112520352-Azidophenol2회HCID 113670133-AzidophenolHCID 67207896Tyrosine phenol

생성물 1

HCID 150307902-azido-L-tyrosine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

A solution of 450 mg of m-azidophenol (3.33 mmol), 407 mg pyruvic acid, 1.8 mg of pyridoxal-5'-phosphate, 711 mg of ammonium acetate and 10 units of tyrosine phenol lyase in 74 ml of water was adjusted to pH 8 with dilute NH4OH and stored in the dark at room temperature for 4 d. The mixture was then acidified with dilute acetic acid and filtered through celite. The filtrate was extracted two times with 50 ml of ethyl acetate to remove unreacted azidophenol [200 mg (1.48 mmol) azidophenol was recovered]. An Amberlite IRA-118H column (1.5×10 cm) activated with 2N HCl and washed with water. The reaction mixture was passed through the column and eluted with 4% NH4OH. The fractions that gave a positive ninhydrin reaction after spotting on silica gel plates were combined and lyophilized to give compound 1, 2-azido-L-tyrosine, as a white solid. Recrystallization from water gave 225 mg (1.01 mmol) of analytically pure 1, mp 200°-210° C. (decomp), [α]D23 -8.62 (C=4, 1N HCl), IR (KBr) cm-1 3700-2600, 2110, 1605, UV (H2O) λmax 219, 250, 290, ms (Cl NH3): 223 (M+1)+, 179 (M-COOH+1)+, 149 [HOPhN3 (CH3)]+, 1H NMR (D2O) 8 2.93 (1H, dd, J1 =14.5 Hz, J2 =8.2 Hz) , 3.20 (1H, dd, J1 =14.5 Hz, J2 =5.3 Hz) , 3.94 (1H, dd, J1 =8.2 Hz, J2 =5.3 Hz), 6.64 (1H, dd, J1 =8.3 Hz, J2 =2 Hz) , 6.75 (1H, d, J=2 Hz), 7.12 (H, d, J=8.3 Hz).

후처리

  1. customdark at room temperature
  2. customfor 4 d
  3. filtrationfiltered through celite
  4. extractionThe filtrate was extracted two times with 50 ml of ethyl acetate
  5. washwashed with water
  6. washeluted with 4% NH4OH
  7. customThe fractions that gave

출처 및 근거

ORD 기록
ord-653718384612436aa44d61d6c0510916
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05276170

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