5-Fluoro-d-tryptophan

Base Information

• Chemical Name: 5-Fluoro-d-tryptophan
• CAS No.: 97749-24-1
• Molecular Formula: C₁₁H₁₁FN₂O₂
• Molecular Weight: 222.219
• Hs Code.: 2933998090
• UNII: 7X85O74VU5
• DSSTox Substance ID: DTXSID10350886
• Nikkaji Number: J232.143B
• Mol file: 97749-24-1.mol

Synonyms:5-fluoro-d-tryptophan;97749-24-1;D-Tryptophan, 5-fluoro-;(R)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid;D-5-fluorotryptophan;(2R)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid;5-Fluorotryptophan, D-;7X85O74VU5;SCHEMBL249955;UNII-7X85O74VU5;DTXSID10350886;MFCD06797666;AKOS015911051;CS-0314380;5-Fluoro-D-tryptophan (H-DL-Trp(5-F)-OH);A50269;F-6835;Q27268979;(R)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoicacid

Chemical Property of 5-Fluoro-d-tryptophan

Chemical Property:

• PSA: 79.11000
• LogP: 1.96170
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 222.08045576
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

99% ^*data from raw suppliers

5-Fluoro-D-Tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1F)C(=CN2)CC(C(=O)O)N
• Isomeric SMILES: C1=CC2=C(C=C1F)C(=CN2)C[C@H](C(=O)O)N

Technology Process of 5-Fluoro-d-tryptophan

There total 26 articles about 5-Fluoro-d-tryptophan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

Nα-acetyl-5-fluoro-D,L-tryptophan (7303-54-0) → Nα-acetyl-5-fluoro-D-tryptophan (320581-74-6) + 5-fluoro-L-tryptophan (16626-02-1,343-91-9,97749-24-1)

Guidance literature:

With borate buffer; cobalt(II) chloride; at 37 ℃; for 48h; pH=8.0; Enzymatic reaction;

DOI:10.1016/j.tetlet.2008.02.120

Reference yield: 84.0%

ethyl 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoate (154170-01-1) → DL-5-fluorotryptophan (154-08-5,343-91-9,97749-24-1)

Guidance literature:

With potassium hydroxide; In methanol; water;

DOI:10.1074/jbc.M116.741561

Reference yield: 83.0%

5-fluoro-1H-indole (399-52-0) + L-serin (56-45-1,83245-15-2) → 5-fluoro-L-tryptophan (16626-02-1,343-91-9,97749-24-1)

Guidance literature:

With Escherichia coli/pSTB₇ tryptophan synthase; pyridoxal 5'-phosphate; at 37 ℃; for 72h; aq. phosphate buffer;

DOI:10.1016/j.bmcl.2008.07.053

upstream raw materials:

acetylamino-(5-fluoro-indol-3-ylmethyl)-malonic acid

acetylamino-(5-fluoro-indol-3-ylmethyl)-malonic acid diethyl ester

acetylamino-[3-(4-fluoro-phenylhydrazono)-propyl]-malonic acid diethyl ester

3-dimethylaminomethyl-5-fluoroindole

Downstream raw materials:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)-propanoic acid

(2S)-N-((3S,6S)-3-(tert-butyl)-1⁹-fluoro-2⁴-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-1^5a,1^10bdihydro-1⁶H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide

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