α‑Hydroxyl‑ω‑Thiol‑poly(L‑lactide) (PLLA‑SH, MW 2K) is linear, mono‑thiol‑terminated semi‑crystalline biodegradable aliphatic polyester. Its backbone is assembled from stereoregular L‑lactide repeating units, exhibiting intrinsic semi‑crystallinity which differentiates it from fully‑amorphous PDLLA. As low‑molecular‑weight thiol‑functional PLLA derivative, this 2 kDa grade shows low hydrophobicity and relatively fast homogeneous hydrolytic degradation. One polymer terminus bears reactive thiol (‑SH) group, the opposite terminus retains inert hydroxyl (‑OH). Terminal thiol can undergo thiol‑ene click reaction, disulfide bond formation, and conjugate with maleimide, gold surface, pyridyl disulfide moieties under mild conditions, achieving covalent modification with targeting ligands and biomolecules. It acts as monofunctional thiol‑containing building block for fast‑degrading nanoparticle fabrication, surface sulfhydryl modification and biodegradable biomedical delivery research.
Key Features
- MW: 2000 Da, linear α‑hydroxyl‑ω‑thiol‑terminated poly(L‑lactide)
- Semi‑crystalline stereoregular L‑lactide structure, distinct from amorphous PDLLA
- Low hydrophobicity, relatively fast and uniform hydrolytic degradation versus higher‑MW PLLA‑SH homologues
- Excellent biocompatibility; degrades into non‑toxic L‑lactic acid in vitro and in vivo
- Single terminal thiol (‑SH) reactive group for thiol‑ene, thiol‑maleimide coupling and disulfide cross‑linking; opposite polymer end is inert hydroxyl ‑OH
- Narrow molecular‑weight distribution, stable batch‑to‑batch reproducibility; high thiol end‑group functionality
- Soluble in DCM, CHCl₃, THF, DMF, acetone; insoluble in water
- Thiol‑terminated polymer; sensitive to oxygen and heavy‑metal ions; avoid prolonged air exposure; sealed inert‑gas storage required
Applications
- Monofunctional thiol‑containing building block for maleimide‑modified ligand conjugation, thiol‑ene click chemistry
- Preparation of thiol‑functional fast‑degrading PLLA nanoparticles and micelles for drug‑delivery research
- Sulfhydryl surface modification of polyester materials for gold‑nanoparticle immobilization and disulfide cross‑linking
- Precursor for disulfide‑linked redox‑responsive degradable polymer conjugates
- Research‑grade raw material for redox‑sensitive biomedical polymer study
Handling & Storage
- Store at −20 °C under dry inert nitrogen or argon atmosphere; strictly moisture‑proof, minimize oxygen exposure
- Keep hermetically sealed; oxygen may oxidize thiol groups to disulfide and humidity accelerates polyester hydrolysis; avoid repeated freeze‑thaw cycles
- For research‑only use; not intended for clinical or diagnostic applications
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