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Fmoc-D-serine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

N-Fmoc-D-serine is an N-Fmoc-protected form of D-Serine. D-Serine is a neurotransmitter that is concentrated in the mammalian brain, and is one of the very few amino acids that occur in the D- and L-configurations in significant amounts. D-Serine is a potent agonist of the N-methyl-D-aspartate (NMDA) receptor in the brain, which is associated with schizophrenia. Use of D-Serine has been considered as an additional therapy for refractory schizophrenic patients.

Category

Fmoc-Amino Acids

Catalog number

BAT-003722

CAS number

116861-26-8

Molecular Formula

C18H17NO5

Molecular Weight

327.30

Specification
Reference Reading

IUPAC Name

(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropanoic acid

Synonyms

Fmoc-D-Ser-OH; Fmoc-D-β-Hydroxyalanine; (R)-Fmoc-2-amino-3-hydroxypropionic acid

Appearance

White to off-white powder

Purity

≥ 98% (HPLC)

Density

1.362±0.06 g/cm3

Melting Point

96-101 °C

Boiling Point

599.3±50.0 °C

Storage

Store at 2-8 °C

InChI

InChI=1S/C18H17NO5/c20-9-16(17(21)22)19-18(23)24-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16,20H,9-10H2,(H,19,23)(H,21,22)/t16-/m1/s1

InChI Key

JZTKZVJMSCONAK-MRXNPFEDSA-N

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CO)C(=O)O

1."O-acyl isopeptide method" for peptide synthesis: synthesis of forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH.

Yoshiya T1, Taniguchi A, Sohma Y, Fukao F, Nakamura S, Abe N, Ito N, Skwarczynski M, Kimura T, Hayashi Y, Kiso Y. Org Biomol Chem. 2007 Jun 7;5(11):1720-30. Epub 2007 Apr 25.

The O-acyl isopeptide method has recently received attention as an efficient synthetic method for peptides. Herein, forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH (1-40) were effectively synthesized in two-steps without epimerization. The O-acyl isodipeptide units are important building blocks to enable the routine use of the O-acyl isopeptide method.