Fmoc-Thr[GalNAc(Ac)3-α-D]-OH

Names

[ Name ]:
Fmoc-Thr[GalNAc(Ac)3-α-D]-OH

[Synonym ]:
FMOC-THR(GALNAC(AC)3-α-D)-OH
α-D-Galactopyranoside, (1R,2S)-2-carboxy-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1-methylethyl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate
(2R,3R)-3-{[(2S,3R,4R,5R,6R)-3-Acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoic acid (non-preferred name)
(2S,3R)-3-{[(2S,3R,4R,5R,6R)-3-Acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoic acid
α-D-Galactopyranoside, (1R,2R)-2-carboxy-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1-methylethyl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate
Fmoc-Thr[GalNAc(Ac)3-α-D]-OH

Biological Activity

[Description]:

Fmoc-Thr[GalNAc(Ac)3-α-D]-OH i a building block in the development of cancer vaccine.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Peptides

[In Vitro]

The O-glycosidic linkage and the O-acetyl protection in this building block is stable to both piperidine and TFA, making it completely compatible with standard protocols in Fmoc solid phase peptide synthesis. The Tn antigen is a tumor-associated carbohydrate antigen that is not normally expressed in peripheral tissues or blood cells. Expression of this antigen, which is found in a majority of human carcinomas of all types, arises from a blockage in the normal O-glycosylation pathway in which glycans are extended from the common precursor GalNAcα1-O-Ser/Thr (Tn +antigen). This precursor is generated in the Golgi apparatus on newly synthesized glycoproteins by a family of polypeptide α- N-acetylgalactosaminyltransferases (ppGalNAcTs) and then extended to the common core 1 O-glycan Galβ1-3GalNAcα1-OSer/Thr (T antigen) by a single enzyme termed the T-synthase (core 1 β3-galactosyltransferase or C1GalT). Formation of the active form of the T-synthase requires a unique molecular chaperone termed Cosmc, encoded by Cosmc on the X-chromosome[1].

[References]

[1]. Ju T, et al. The Cosmc connection to the Tn antigen in cancer. Cancer Biomark. 2014 Jan 1;14(1):63-81.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
857.1±65.0 °C at 760 mmHg

[ Melting Point ]:
178-183 °C

[ Molecular Formula ]:
C₃₃H₃₈N₂O₁₃

[ Molecular Weight ]:
670.660

[ Flash Point ]:
472.1±34.3 °C

[ Exact Mass ]:
670.237366

[ PSA ]:
202.09000

[ LogP ]:
4.58

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.592

[ Storage condition ]:
-15°C

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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