H-Phe-OBzl.TosOH
H-Phe-OBzl.TosOH, or L-phenylalanine benzyl ester p-toluenesulfonate (CAS 1738-78-9), is the tosylate salt of the benzyl ester of L-phenylalanine. It is a white crystalline solid with good storage stability when kept dry, and it is soluble in polar aprotic and alcoholic solvents such as dimethylformamide, dimethyl sulfoxide, methanol and dichloromethane, and only sparingly soluble in water. The benzyl ester protects the carboxyl group during peptide bond formation and is removed selectively by catalytic hydrogenolysis without affecting most other protecting groups, while the tosylate counter-ion makes the salt crystalline, non-volatile and far more convenient to handle than the free amino ester. The aromatic side chain also provides a useful ultraviolet chromophore for chromatographic detection.
1. Peptide synthesis: supplies the L-phenylalanine residue as a protected, readily weighed ester for solution and solid-phase peptide assembly and for fragment condensation strategies in research and manufacturing.
2. Chiral building block: used in the synthesis of peptidomimetics, enzyme inhibitors, renin and HIV protease inhibitors, opioids and other active pharmaceutical ingredients requiring an enantiopure phenylalanine unit.
3. Protecting-group orthogonality: the benzyl ester is compatible with Boc, Fmoc and tert-butyl chemistry and is cleaved under mild hydrogenolysis conditions, allowing selective deprotection in multistep routes and enabling convergent synthesis of complex peptides.
4. Handling and storage: store in a cool, dry, well-ventilated place in tightly closed containers away from oxidising agents; avoid dust generation and note that the ester is hydrolysed under strongly basic conditions, so it should not be exposed to concentrated alkali or extended contact with amines.
Product Name: H-Phe-OBzl.TosOH
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