*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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 !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation 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%. |
Yield | Reaction Conditions | Operation 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%. |