LL dipeptide zwitterion

Base Information

• Chemical Name: LL dipeptide zwitterion
• CAS No.: 3303-31-9
• Molecular Formula: C12H24N2O3
• Molecular Weight: 244.334
• Hs Code.: 2924199090
• Mol file: 3303-31-9.mol

Synonyms:LL zwitterion;Leu-Leu zwitterion;LL dipeptide zwitterion;L-Leu-L-Leu zwitterion;L-leucyl-L-leucine zwitterion;SCHEMBL17831230;CHEBI:191208

Chemical Property of LL dipeptide zwitterion

Chemical Property:

• Melting Point: 270-272℃ (decomposition)
• Boiling Point: 432.7°Cat760mmHg
• Flash Point: 215.5°C
• PSA: 92.42000
• Density: 1.051g/cm³
• LogP: 2.06650
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly, Heated), Water (Slightly, Sonicated)
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 244.17869263
• Heavy Atom Count: 17
• Complexity: 259

Purity/Quality:

99% ^*data from raw suppliers

Leu-Leu-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NC(CC(C)C)C(=O)[O-])[NH3+]
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)[O-])[NH3+]

Technology Process of LL dipeptide zwitterion

There total 41 articles about LL dipeptide zwitterion 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: 99.6%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → L-leucyl-L-leucine (3303-31-9)

Guidance literature:

N-tert-butoxycarbonyl-L-leucine; at 50 ℃; Ionic liquid; Inert atmosphere;

With water; sodium hydroxide; In tetrahydrofuran;

N-tert-butoxycarbonyl-L-leucine; Temperature; Further stages;

Reference yield: 91.0%

Fmoc-Leu-OH (35661-60-0) → L-leucyl-L-leucine (3303-31-9)

Guidance literature:

Fmoc-Leu-OH; With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

With piperidine; In N,N-dimethyl-formamide; for 0.333333h;

Fmoc-Leu-OH; Further stages;

DOI:10.1080/00397911.2016.1141428

Reference yield:

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → Val-Val (3918-94-3) + L-leucyl-L-leucine (3303-31-9) + L-valinyl-L-valinyl-L-valine (28130-13-4) + L-leucyl-L-leucyl-L-leucine (10329-75-6)

Guidance literature:

With magnesium sulfate heptahydrate; C-terminal His-tagged Bacillus subtilis NBRC₃₁₃₄ L-amino acid ligase RizB; ATP; at 30 ℃; for 20h; pH=8; aq. Tris-HCl buffer; Enzymatic reaction;

DOI:10.1271/bbb.90649

upstream raw materials:

(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoic acid

N-(N-allyloxycarbonyl-L-leucyl)-L-leucine

Cbz-L-Leu-L-Leu-OMe

N-benzyloxycarbonyl-L-leucyl-L-leucine

Downstream raw materials:

benzenesulfonamide

carbon dioxide

isovaleraldehyde

Z-Leu-Leu-Leu-[methyl (3RS,4RS)-3,4-epoxypiperidine-3-carboxylate]

Refernces

Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(αMe)Phe as catalyst

10.1016/S0957-4166(97)00178-X

The research investigates the catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-dipeptides based on His and the unnatural (αMe)Phe as catalysts. The LL dipeptide, specifically cyclo-[L-His-L-(αMe)Phe] (15), is a key catalyst in the study. It is a cyclic dipeptide composed of L-histidine (His) and L-(α-methyl)phenylalanine ((αMe)Phe). This compound is synthesized through a series of chemical reactions starting from L-(αMe)Phe and L-histidine, involving protection, coupling, and cyclization steps. The LL dipeptide 15 is notable for its conformational rigidity, which is attributed to the incorporation of the unnatural (αMe)Phe residue. This rigidity is crucial for its catalytic activity in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde. The study demonstrates that 15 achieves high enantiomeric excesses (up to 99% e.e. for benzaldehyde and 89% e.e. for p-methoxybenzaldehyde derivatives) at low temperatures (-40°C) with excellent yields (98% and 93%, respectively). NMR studies suggest that the orientation of the aldehyde in the reaction complex with 15 is different from the Tanaka model, with the aldehyde hydrogen-bonded to the NH of the (αMe)Phe residue rather than the histidine residue.