O-Benzyl-L-serine
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O-Benzyl-L-serine

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Category
L-Amino Acids
Catalog number
BAT-004165
CAS number
4726-96-9
Molecular Formula
C10H13NO3
Molecular Weight
195.20
O-Benzyl-L-serine
IUPAC Name
(2S)-2-amino-3-phenylmethoxypropanoic acid
Synonyms
L-Ser(Bzl)-OH; (S)-2-Amino-3-(Benzyloxy)Propanoic Acid
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.217 g/cm3
Melting Point
~227 °C (dec.)
Boiling Point
359.1°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H13NO3/c11-9(10(12)13)7-14-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/m0/s1
InChI Key
IDGQXGPQOGUGIX-VIFPVBQESA-N
Canonical SMILES
C1=CC=C(C=C1)COCC(C(=O)O)N
3. Synthesis of water-soluble poly(α-hydroxy acids) from living ring-opening polymerization of O-benzyl-L-serine carboxyanhydrides
Yanbing Lu, Lichen Yin, Yanfeng Zhang, Zhang Zhonghai, Yunxiang Xu, Rong Tong, Jianjun Cheng ACS Macro Lett. 2012 Apr 17;1(4):441-444. doi: 10.1021/mz200165c.
O-benzyl-L-serine carboxyanhydrides were synthesized via diazotization of O-benzyl-L-serine with sodium nitrite in aqueous sulfuric acid solution followed by cyclization of the resulting serine-based α-hydroxy acid with phosgene. Degradable, water-soluble poly(α-hydroxy acids) bearing pendant hydroxyl groups were readily prepared under mild conditions via ring-opening polymerization of O-benzyl-L-serine carboxyanhydrides followed by removal of the benzyl group and showed excellent cell compatibility, suggesting their potential being used as novel materials in constructing drug delivery systems and as hydrogel scaffolds for tissue engineering applications.
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