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Fmoc-L-serine

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

N-Fmoc-L-serine is an N-Fmoc-protected form of L-Serine. L-Serine is a non-essential amino acid that is required for the synthesis of sphingolipids and phosphatidylserine, compounds that are important for central nervous system neuronal survival. L-Serine is also important in intermediary metabolism in eukaryotic cells.

Category

Fmoc-Amino Acids

Catalog number

BAT-003845

CAS number

73724-45-5

Molecular Formula

C18H17NO5

Molecular Weight

327.30

Specification
Reference Reading

IUPAC Name

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

Synonyms

Fmoc-L-Ser-OH; Fmoc-L-β-hydroxyalanine(S)-Fmoc-2-amino-3-hydroxypropionic acid; FMOC-SER-OH; N-Fmoc-L-serine-OH; N-FMOC-L-SERINE; FMOC-SERINE; FMOC-SER

Appearance

White powder

Purity

≥ 99.5% (Chiral HPLC)

Density

1.362±0.06 g/cm3

Melting Point

~ 95 °C

Boiling Point

599.3±50.0 °C

Storage

Store at RT

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-/m0/s1

InChI Key

JZTKZVJMSCONAK-INIZCTEOSA-N

Canonical SMILES

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

1.Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters.

Carvalho I1, Scheuerl SL, Ravindranathan Kartha KP, Field RA. Carbohydr Res. 2003 May 1;338(10):1039-43.

Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding beta-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding beta-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).