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Chemical Structure| 6404-29-1 Chemical Structure| 6404-29-1
Chemical Structure| 6404-29-1

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CAS No.: 6404-29-1

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Boc-ε-Acp-OH is a Boc-protected amino acid derivative, commonly used in the synthesis of peptides and in the preparation of amino acid analogs.

Synonyms: Boc-6-aminohexanoic acid

4.5 *For Research Use Only !

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Product Citations

Product Citations

Rathje, Oliver H. ; Perryman, Lara ; Payne, Richard J. ; Hamprecht, Dieter W. ;

Abstract: Mixed Lineage Kinase domain-Like pseudokinase (MLKL) is implicated in a broad range of diseases due to its role as the ultimate effector of necroptosis and has therefore emerged as an attractive drug target. Here, we describe the development of PROteolysis TArgeting Chimeras (PROTACs) as a novel approach to knock down MLKL through chem. means. A series of candidate degraders were synthesized from a high-affinity pyrazole carboxamide-based MLKL ligand leading to the identification of a PROTAC mol. that effectively degraded MLKL and completely abrogated cell death in a TSZ model of necroptosis. By leveraging the innate ability of these PROTACs to degrade MLKL in a dose-dependent manner, the quant. relationship between MLKL levels and necroptosis was interrogated. This work demonstrates the feasibility of targeting MLKL using a PROTAC approach and provides a powerful tool to further our understanding of the role of MLKL within the necroptotic pathway.

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Product Details of Boc-ε-Acp-OH

CAS No. :6404-29-1
Formula : C11H21NO4
M.W : 231.29
SMILES Code : C(=O)(OC(C)(C)C)NCCCCCC(=O)O
Synonyms :
Boc-6-aminohexanoic acid
MDL No. :MFCD00037798
InChI Key :RUFDYIJGNPVTAY-UHFFFAOYSA-N
Pubchem ID :637602

Safety of Boc-ε-Acp-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Boc-ε-Acp-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6404-29-1 ]

[ 6404-29-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 580-15-4 ]
  • [ 6404-29-1 ]
  • [ 960129-44-6 ]
YieldReaction ConditionsOperation in experiment
56% With C15H23N3Pol(1+)*Cl(1-); benzotriazol-1-ol; In dichloromethane; at 35℃; Example 2a; N-(Quinolin-6-yl)-6-(sulfamoylamino)hexanamide (5a) Step 1: tert-Butyl 6-oxo-6-(quinolin-6-ylamino)hexylcarbamate (1a) To a solution of N-Boc caproic acid (0.23 g, 1.0 mmol) in DCM (5 ml) was added PS-carbodiiminde (0.8 g, 1.1 mmol). After 10 minutes <strong>[580-15-4]6-aminoquinoline</strong> (0.1 g, 0.7 mmol) and HOBt (0.13 g, 1.0 mmol) were added and stirred over night at 35 C. The mixture was filtered and concentrated. The residue was purified by silica gel column chromatography with gradient of EtOAc (20-100%) in Hexane to afford 1a (0.2 g, 56%) as a beige solid. LRMS (ESI): (calc.) 357.2; (found) 358.3 (MH)+.
  • 2
  • [ 7724-12-1 ]
  • tert-butyl 6-(2-cyanobenzo[d]thiazol-6-ylamino)-6-oxohexylcarbamate [ No CAS ]
  • [ 6404-29-1 ]
  • [ 543-27-1 ]
  • 4-(6-(2-cyanobenzo[d]thiazol-6-ylamino)-6-oxohexylcarbamoyl)-2-(3-(dimethylamino)-6-(dimethyliminio)-6H-xanthen-9-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; methoxybenzene; acetonitrile; Part E. Synthesis of 4-(6-(2-cyanobenzo[d]thiazol-6-ylamino)-6-oxohexylcarbamoyl)-2-(3-(dimethylamino)-6-(dimethyliminio)-6H-xanthen-9-yl)benzoate (compound 3082) 6-(tert-Butoxycarbonylamino)hexanoic acid (316 mg) was mixed with anhydrous THF (10 mL), <strong>[7724-12-1]6-aminobenzo[d]thiazole-2-carbonitrile</strong> (200 mg), iso-butylchloroformate (193 muL), and N-methylmorpholine (314 muL) at -4° C. The reaction was allowed to stir overnight at RT. The reaction was partitioned between ethyl acetate and bicarbonate. The ethyl acetate layer was evaporated, and the residue was eluted through silica with heptane: ethyl acetate (1:2). Yield 354 mg. tert-Butyl 6-(2-cyanobenzo[d]thiazol-6-ylamino)-6-oxohexylcarbamate (350 mg) was added to cold (0° C.) solution of dichloromethane (4 mL), trifluoroacetic acid (4 mL), and anisole (400 muL). After 135 minutes, the majority of solvent was evaporated, and 10 mL acetonitrile and 30 mL of diethyl ether was added. The mixture was allowed to sit overnight. The precipitate was isolated and used without further purification.
  • 3
  • [ 6404-29-1 ]
  • [ 35661-51-9 ]
  • [ 151890-12-9 ]
YieldReaction ConditionsOperation in experiment
79% A solution of Boc-Ahx-OH (1.29 g, 5.58 mmol), HOBt (1.02 g, 6.66 mmol), HBTU (2.54 g, 6.66 mmol) and DIEA (2.44 niL, 14.0 mmol) in anhydrous DMF (10 mL) was stirred at ambient temperatures under nitrogen for 20 minutes, and treated with 9-fluorenylmethyl carbazate (1.42 g, 5.58 mmol) and DIEA (0.5 mL, 2.87 mmol). The solution was stirred for 3.5 hours, diluted with dichloromethane (30 mL), washed consecutively with 10percent citric acid (50 mL), saturated NaHCO3 (3 X 50 mL), and saturated NaCl (3 X 50 mL), dried over MgSO4, filtered, and concentrated to give a yellow oil. The oil was purified by flash chromatography over silica gel, eluting with 2:1 ethyl acetate:hexanes to give the title compound as a colorless solid (2.061 g, 79percent, HPLC purity 100percent). 1H NMR (CDCl3): delta 7,75 (d, J= 7.5 Hz, 2H), 7.58 (d, J= 7.4 Hz, 2H), 7.50 (br, IH), 7.39 (t, J= 7.4 Hz, 2H), 7.30 (dt, J- 7.0 Hz, 2H), 6.87 (br, IH), 4.63 (s, IH), 4.44 (d, J= 6.9 Hz, 2H), 4.24 (t, J= 7.1 Hz, IH), 3.08 (s, 2H), 2.23 (s, 2H), 1.68 (m, 2H), 1.42 (s, 9H), 1.47-1.35 (m, 4H); 13C NMR (CDCI3): delta 172.6, 171.2, 156.2, 143.5, 141.3, 127.9, 127.8, 127.1, 125.1, 124.9, 120.0, 79.2, 68.0, 60.4, 46.9, 40.2, 33.8, 29.6, 28.4, 26.0, 24.7, 21.1, 14.2. MS (ESI): 368.4(100, M-Boc+H).
  • 4
  • [ 7724-12-1 ]
  • [ 6404-29-1 ]
  • tert-butyl 6-(2-cyanobenzo[d]thiazol-6-ylamino)-6-oxohexylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
354 mg With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -4 - 20℃; 6-(tert-Butoxycarbonylamino)hexanoic acid (316 mg) was mixed with anhydrous THF (10 mL), <strong>[7724-12-1]6-aminobenzo[d]thiazole-2-carbonitrile</strong> (200 mg), iso-butylchloroformate (193 muL), and N-methylmorpholine (314 muL) at ?4° C. The reaction was allowed to stir overnight at RT. The reaction was partitioned between ethyl acetate and bicarbonate. The ethyl acetate layer was evaporated, and the residue was eluted through silica with heptane: ethyl acetate (1:2). Yield 354 mg.
354 mg With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; at -4 - 20℃; 6-(tert-Butoxycarbonylamino)hexanoic acid (316 mg) was mixed with anhydrous THF (10 mL), <strong>[7724-12-1]6-aminobenzo[d]thiazole-2-carbonitrile</strong> (200 mg), iso-butylchloroformate (193 muL), and N-methylmorpholine (314 muL) at ?4° C. The reaction was allowed to stir overnight at RT. The reaction was partitioned between ethyl acetate and bicarbonate. The ethyl acetate layer was evaporated, and the residue was eluted through silica with heptane: ethyl acetate (1:2). Yield 354 mg.
  • 5
  • [ 7724-12-1 ]
  • [ 6404-29-1 ]
  • 6-amino-N-(2-cyanobenzo[d]thiazol-6-yl)hexanamide [ No CAS ]
  • 6
  • [ 745017-94-1 ]
  • [ 6404-29-1 ]
  • C50H84N6O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% 6-((tert-butoxycarbonyl)amino)hexanoic acid (46.5 mg,0.201 mmol) was dissolved in DMSO (1 mE) and Huenig?s Base (0.08 mE, 0.458 mmol) and HATU (76 mg, 0.201 mmol) were added. The reaction stirred at RT for 30 minutes before adding the reaction mixture to MMAF (50 mg, 0.067 mmol). The reaction then stirred at RT for 4 hours. The reaction mixture was loaded directly onto 35 g c-i 8 colunm for purification by column chromatography (5-75percent MeCN/Water 0.1percent formic acid). The solvent was removed on rotovap and placed on high vac overnight.The resulting product was treated with TFA (2 mE) at 00 C. and brought to room temp to stir for 5 mm. The reaction was loaded directly onto a 35 g C-18 colunm for column purification. The solvent was removed under reduced pressure toyield 30 mg (52percent yield).
  • 7
  • [ 6404-29-1 ]
  • [ 123639-61-2 ]
  • Fmoc-L-Hyp(Bzl)-OH [ No CAS ]
  • [ 159766-56-0 ]
  • C43H61N5O11 [ No CAS ]
 

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