H-Ser(tBu)-OH, with the CAS number 18822-58-7, is a protected derivative of the essential amino acid L-serine, also called O-tert-Butyl-L-serine. Its molecular formula is C₇H₁₅NO₃, and molecular weight is 161.20 g/mol. It has a tert-butyl (tBu) protecting group attached to L-serine’s hydroxyl group, retaining the L-configuration and inherent biochemical activity while avoiding unwanted side reactions, thus being widely used in peptide synthesis, pharmaceutical research, and biochemistry.
Physically, it appears as a white to off-white crystalline powder or granular solid, with a melting point of ~230-235℃ (decomposition). It is slightly soluble in cold water, more soluble in hot water, and readily soluble in organic solvents like methanol, ethanol, and dimethylformamide. Optically active, its specific rotation [α]²⁰/D ranges from -12.0° to -16.0° (in water, c=2). It has low hygroscopicity and good stability under normal conditions, facilitating handling, storage, and formulation.
Chemically, the tert-butyl protecting group is its key feature, shielding the hydroxyl group during peptide bond formation to ensure selective reactivity of α-amino and carboxyl groups. It can be easily cleaved under mild acidic conditions (e.g., trifluoroacetic acid) without damaging peptide chains, compatible with standard peptide synthesis protocols. It is stable in neutral and weakly alkaline environments but may deplete under strong acid or high temperatures.
Its core application is as a building block in peptide synthesis, used for complex peptides like therapeutic peptides, peptide hormones, and enzyme inhibitors. The protected hydroxyl group prevents side reactions (esterification, oxidation) to ensure product purity and structural integrity. It also serves as a pharmaceutical intermediate and biochemical reagent for studying amino acid metabolism and enzyme activity.
Safety-wise, it is generally recognized as safe (GRAS) under normal handling, with mild irritation potential. It should be stored in a sealed, cool, dry, dark environment at 2-8℃, away from oxidants, moisture, and high temperatures. With excellent protectiveness and biocompatibility, it is indispensable in peptide chemistry and pharmaceutical development.
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