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Chemical Structure| 193887-44-4 Chemical Structure| 193887-44-4
Chemical Structure| 193887-44-4

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Fmoc-β-HoLeu-OH is a leucine derivative that serves as a standard structural unit for amino acid residues in peptide synthesis.

Synonyms: Fmoc-β-HoLeu-OH

4.5 *For Research Use Only !

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Product Details of Fmoc-β-HoLeu-OH

CAS No. :193887-44-4
Formula : C22H25NO4
M.W : 367.44
SMILES Code : CC(C)C[C@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CC(O)=O
Synonyms :
Fmoc-β-HoLeu-OH
MDL No. :MFCD01863059
InChI Key :YLVSABQQLLRFIJ-HNNXBMFYSA-N
Pubchem ID :2761527

Safety of Fmoc-β-HoLeu-OH

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

Application In Synthesis of Fmoc-β-HoLeu-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 [ 193887-44-4 ]

[ 193887-44-4 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 193954-28-8 ]
  • (R)-β3-homovalyl-(S)-β3-homoalanyl-(S)-β3-homoleucyl-(S)-β3-homophenylalanyl-(R)-β3-homovalyl-(S)-β3-homoalanyl-(S)-β3-homoleucine [ No CAS ]
  • 2
  • [ 172695-33-9 ]
  • [ 76-05-1 ]
  • [ 187089-29-8 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • (S)-3-[(S)-3-((R)-3-{(S)-2-[(S)-3-((R)-3-Amino-4-methyl-pentanoylamino)-butyrylamino]-4-methyl-pentane-1-sulfonylamino}-4-methyl-pentanoylamino)-butyrylamino]-5-methyl-hexanoic acid amide; compound with trifluoro-acetic acid [ No CAS ]
  • 3
  • [ 172695-33-9 ]
  • [ 76-05-1 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 217633-70-0 ]
  • C51H97N9O10S*C2HF3O2 [ No CAS ]
  • 4
  • [ 172695-33-9 ]
  • [ 76-05-1 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 311330-41-3 ]
  • C50H96N10O10S*C2HF3O2 [ No CAS ]
  • 5
  • [ 172695-33-9 ]
  • [ 76-05-1 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • H-(S)-β3-HVal-(S)-β3-HAla-(S)-β3-Hleu-(S)-β3-HVal-(S)-β3-HAla-(S)-β3-HLeu-NH2 * trifluoroacetic acid [ No CAS ]
  • 6
  • [ 172695-33-9 ]
  • [ 76-05-1 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • H-(S)-β3-HVal-(S)-β3-HAla-(S)-β3-HLeu-(S)-β3-HVal-(S)-β3-HAla-(S)-β3-HLeu-(S)-β3-HVal(S)-β3-HAla-(S)-β3-HLeu-NH2 * trifluoroacetic acid [ No CAS ]
  • 7
  • [ 76-05-1 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 193693-60-6 ]
  • Fmoc-β3-HGln-OH [ No CAS ]
  • Fmoc-β3-HIle-OHFmoc-β3-HLys(Boc)-OH [ No CAS ]
  • H2N-β3-HCys-β3-HAsp-β3-HTyr-β3-HIle-β3-HLys-β3-HGln-β3-HLeu-β3-HAla-β3-HSer-β3-HPhe-β3-HPro-OH trifluoroacetate [ No CAS ]
  • 8
  • [ 172695-33-9 ]
  • [ 76-05-1 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 193954-28-8 ]
  • Fmoc-β3-HLys(Boc)-OHFmoc-protected-β3-HSer [ No CAS ]
  • H2N-β3-HAla-β3-HThr-β3-HLys-β3-HVal-β3-HPhe-β3-HSer-β3-HLeu-β3-HPhe-β3-HLys-β3-HAla-S-ethylpropanoate trifluoroacetate [ No CAS ]
  • 9
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 346610-79-5 ]
  • [ 359586-64-4 ]
  • C67H115N17O12 [ No CAS ]
  • 10
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 346610-79-5 ]
  • [ 359586-64-4 ]
  • C64H109N19O12 [ No CAS ]
  • 11
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 193954-28-8 ]
  • [ 209252-17-5 ]
  • [ 193954-27-7 ]
  • [ 203854-47-1 ]
  • Boc-β3-HCys(Trt)-OH [ No CAS ]
  • CF3CO2H*H2N-β(3)hCys-β(3)hAla-β(3)hLeu-β(3)hLys-β(3)hLeu-β(3)hPhe-β(3)hAsp-β(3)hVal-β(3)hPhe-β(3)hLys-β(3)hAla-β(3)hIle-β(3)hAsp-OH [ No CAS ]
  • 12
  • [ 1135148-98-9 ]
  • [ 108-24-7 ]
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 1188890-05-2 ]
  • 13
  • [ 1135148-98-9 ]
  • [ 108-24-7 ]
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 1188890-10-9 ]
  • 14
  • [ 1135148-98-9 ]
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • (R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-hexanoic acid [ No CAS ]
  • [ 193887-44-4 ]
  • C36H64N6O9 [ No CAS ]
  • 15
  • [ 1135148-98-9 ]
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • (R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-hexanoic acid [ No CAS ]
  • [ 193887-44-4 ]
  • C38H68N6O9 [ No CAS ]
  • 16
  • [ 1135148-98-9 ]
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(4-hydroxyphenyl)butyric acid [ No CAS ]
  • [ 1188890-03-0 ]
  • 17
  • [ 1135148-98-9 ]
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(4-hydroxyphenyl)butyric acid [ No CAS ]
  • [ 1188890-08-5 ]
  • 18
  • [ 125686-90-0 ]
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 209252-17-5 ]
  • [ 193954-27-7 ]
  • [ 203854-51-7 ]
  • [ 203854-49-3 ]
  • [ 203854-47-1 ]
  • [ 1207335-44-1 ]
  • 19
  • [ 35661-38-2 ]
  • [ 35661-60-0 ]
  • [ 86123-10-6 ]
  • [ 35737-15-6 ]
  • [ 94744-50-0 ]
  • [ 172695-33-9 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 193954-27-7 ]
  • [ 203854-49-3 ]
  • [ 203854-47-1 ]
  • N-FMOC-O-tert-butyl-D-threonine [ No CAS ]
  • H-(R)-β3hVal-(S)-β3hGlu-(S)-β3hLeu-(S)-β3hAla-(S)-β3hLys-(R)-β3hIle-(R)-Phe-(R)-Ser-(R)-Leu-Aib-(R)-Trp-(R)-Thr-(R)-Ala-NH2 [ No CAS ]
  • 20
  • [ 1268809-47-7 ]
  • [ 76-05-1 ]
  • [ 193954-26-6 ]
  • [ 193887-44-4 ]
  • [ 193954-27-7 ]
  • [ 1268809-56-8 ]
  • 21
  • [ 71989-31-6 ]
  • [ 86123-10-6 ]
  • [ 109425-55-0 ]
  • [ 193887-44-4 ]
  • [ 203854-59-5 ]
  • C74H118N12O15 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Loading of the HMPB-MBHA-resin: The HMPB-MBHA-resin (theoretical loading=1.2 mmol/g, 2 mmol, 1.67 g) was suspended in 1,2-dichloroethane (10 mL) and concentrated thrice. Then a solution of the first amino acid (5 equiv, 10 mmol), DIC (5 equiv, 10 mmol, 1.54 mL), and DMAP (0.01 equiv, 20 mumol, 3 mg) in dry DCM/DMF (50 mL, 10:1 v/v) was added. The mixture was shaken for 3 h and then drained, washed subsequently with DCM, NMP, DCM, and Et2O. The resin was dried before determination of the loading. The loading procedure was repeated when the loading of the resin was found to be too low.Stepwise elongation: Fmoc-DPhe-HMPB-MBHA-resin (loading of the resin was 0.50 mmol/g, 100 mumol, 200 mg) was submitted to nine cycles of Fmoc solid-phase synthesis with the appropriate commercial amino acid building blocks, or Fmoc-beta2hVal-OH. The side chain of ornithine is protected with a Boc-group. Fmoc removal was effected by treatment with 20% piperidine in NMP for 2×10 min. The resin was subsequently washed with NMP, DCM, MeOH, and finally NMP. Fmoc-AA-OH (2.5 equiv, 250 mumol), HCTU (2.5 equiv, 250 mumol, 103 mg) in NMP was pre-activated for 1 min after the addition of DiPEA (3 equiv, 300 mumol, 53 muL) and then added to the resin. The suspension was shaken for 1.5 h. The resin was washed with NMP, DCM, MeOH, and NMP.Cleavage from the resin: After the final Fmoc deprotection the resin was washed with NMP and DCM and treated with 5 mL 1% TFA in DCM (6×10 min). The filtrates were collected, diluted with toluene (15 mL), and concentrated under reduced pressure. The residue was coevaporated with toluene (2×50 mL).Cyclization: In DMF (80 mL) were dissolved PyBOP (5 equiv, 500 mumol, 260 mg), HOBt (5 equiv, 500 mumol, 77 mg), and DiPEA (15 equiv, 1.5 mmol, 262 muL). The linear decapeptide was dissolved in DMF (5 mL) and added dropwise over 1 h to the reaction mixture. After addition the mixture was stirred for 16 h. The reaction mixture was concentrated in vacuo and the crude mixture was subjected to LH-20 size exclusion chromatography.Boc deprotection: The peptide was dissolved in DCM (2 mL) and TFA (2 mL) was added. The mixture was stirred for 2 h, concentrated, and coevaporated with toluene (2×10 mL). The obtained crude product was applied to preparative HPLC purification. Using gradients of aqueous TFA and acetonitrile the cyclic peptides 1-13 were obtained in the yield range 20-45%.
  • 22
  • [ 71989-31-6 ]
  • [ 86123-10-6 ]
  • [ 109425-55-0 ]
  • [ 193887-44-4 ]
  • [ 203854-59-5 ]
  • (2R)-2-([(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-3-methylbutanoic acid [ No CAS ]
  • C74H116N12O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Loading of the HMPB-MBHA-resin: The HMPB-MBHA-resin (theoretical loading=1.2 mmol/g, 2 mmol, 1.67 g) was suspended in 1,2-dichloroethane (10 mL) and concentrated thrice. Then a solution of the first amino acid (5 equiv, 10 mmol), DIC (5 equiv, 10 mmol, 1.54 mL), and DMAP (0.01 equiv, 20 mumol, 3 mg) in dry DCM/DMF (50 mL, 10:1 v/v) was added. The mixture was shaken for 3 h and then drained, washed subsequently with DCM, NMP, DCM, and Et2O. The resin was dried before determination of the loading. The loading procedure was repeated when the loading of the resin was found to be too low.Stepwise elongation: Fmoc-DPhe-HMPB-MBHA-resin (loading of the resin was 0.50 mmol/g, 100 mumol, 200 mg) was submitted to nine cycles of Fmoc solid-phase synthesis with the appropriate commercial amino acid building blocks, or Fmoc-beta2hVal-OH. The side chain of ornithine is protected with a Boc-group. Fmoc removal was effected by treatment with 20% piperidine in NMP for 2×10 min. The resin was subsequently washed with NMP, DCM, MeOH, and finally NMP. Fmoc-AA-OH (2.5 equiv, 250 mumol), HCTU (2.5 equiv, 250 mumol, 103 mg) in NMP was pre-activated for 1 min after the addition of DiPEA (3 equiv, 300 mumol, 53 muL) and then added to the resin. The suspension was shaken for 1.5 h. The resin was washed with NMP, DCM, MeOH, and NMP.Cleavage from the resin: After the final Fmoc deprotection the resin was washed with NMP and DCM and treated with 5 mL 1% TFA in DCM (6×10 min). The filtrates were collected, diluted with toluene (15 mL), and concentrated under reduced pressure. The residue was coevaporated with toluene (2×50 mL).Cyclization: In DMF (80 mL) were dissolved PyBOP (5 equiv, 500 mumol, 260 mg), HOBt (5 equiv, 500 mumol, 77 mg), and DiPEA (15 equiv, 1.5 mmol, 262 muL). The linear decapeptide was dissolved in DMF (5 mL) and added dropwise over 1 h to the reaction mixture. After addition the mixture was stirred for 16 h. The reaction mixture was concentrated in vacuo and the crude mixture was subjected to LH-20 size exclusion chromatography.Boc deprotection: The peptide was dissolved in DCM (2 mL) and TFA (2 mL) was added. The mixture was stirred for 2 h, concentrated, and coevaporated with toluene (2×10 mL). The obtained crude product was applied to preparative HPLC purification. Using gradients of aqueous TFA and acetonitrile the cyclic peptides 1-13 were obtained in the yield range 20-45%.
  • 23
  • [ 77128-73-5 ]
  • [ 91000-69-0 ]
  • [ 193887-44-4 ]
  • RR-beta-homoleucine-N-methylphenylalanine-NH2 [ No CAS ]
  • 24
  • [ 77128-73-5 ]
  • [ 91000-69-0 ]
  • [ 193887-44-4 ]
  • RR-beta-homoleucine-N-methylphenylalanine [ No CAS ]
  • 25
  • [ 338408-13-2 ]
  • [ 77128-73-5 ]
  • [ 91000-69-0 ]
  • [ 193887-44-4 ]
  • 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,4-triazole-3-carboxamide-R-beta-homoleucine-N-methylphenylalanine-NH2 [ No CAS ]
  • 26
  • [ 338408-13-2 ]
  • [ 77128-73-5 ]
  • [ 193887-44-4 ]
  • (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid [ No CAS ]
  • 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,4-triazole-3-carboxamide-citrulline-beta-homoleucine-N-methylphenylalanine-NH2 [ No CAS ]
 

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