GALACTOSE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H12O6
Molecular Weight	180.1559
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O

InChI

InChIKey=GZCGUPFRVQAUEE-KCDKBNATSA-N

InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C6H12O6
Molecular Weight	180.1559
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26001656 | https://clinicaltrials.gov/ct2/show/NCT02955264 | https://clinicaltrials.gov/ct2/show/NCT00816504 | https://www.ncbi.nlm.nih.gov/pubmed/24997537

Galactose, a monosaccharide sugar, is a key source of energy and is an important compound for early human development. Galactose is present in dairy products, the pectin of some fruits, vegetables, and some herbs. Children get most of their dietary galactose from milk. D-galactose is freely available in health food stores and is promoted for stimulating the immune system and improving gut motility in healthy individuals. Galactose as a part of food supplement participates in phase II of clinical trials for congenital disorders of glycosylation (CDG) patients. CDG is a group of more than 130 inborn errors of metabolism affecting N-linked, O-linked protein and lipid-linked glycosylation. In addition, monosaccharide is used in clinical trials phase I in patients with focal segmental glomerulosclerosis (FSGS), where the galactose lowers the level of a circulating factors that increase glomerular permeability to albumin in patients with resistant FSGS.

Approval Year

PubMed

Title	Date	PubMed
Synthesis and evaluation of novel fluorogenic substrates for the detection of bacterial beta-galactosidase.	2001 Dec	11851821
In vivo fucosylation of lacto-N-neotetraose and lacto-N-neohexaose by heterologous expression of Helicobacter pylori alpha-1,3 fucosyltransferase in engineered Escherichia coli.	2001 Jun	12084982
[Study of ABO blood group secretor type alpha(1,2)-fucosyltransferase gene polymorphism in Chinese].	2002	12645255
Lack of consistency in the associations of Helicobacter pylori seropositivity with Se and Le polymorphisms among Japanese.	2002	12491076
Assignment of FUT8 to chicken chromosome band 5q1.4 and to human chromosome 14q23.2-->q24.1 by in situ hybridization. Conserved and compared synteny between human and chicken.	2002	12438718
Molecular analysis of mutations and polymorphisms of the Lewis secretor type alpha(1,2)-fucosyltransferase gene reveals that Taiwan aborigines are of Austronesian derivation.	2002	11916003
Partial identification by site-directed mutagenesis of a cell growth inhibitory site on the human galectin-1 molecule.	2002	11846886
Transfection of the nm23-H1 gene into human hepatocarcinoma cell line inhibits the expression of sialyl Lewis X, alpha1,3 fucosyltransferase VII, and metastatic potential.	2002 Apr	11935309
Human NK cell-mediated cytotoxicity triggered by CD86 and Gal alpha 1,3-Gal is inhibited in genetically modified porcine cells.	2002 Apr 15	11937533
IgG plasma cells display a unique spectrum of leukocyte adhesion and homing molecules.	2002 Apr 15	11929781
Binding of enzyme IIAGlc, a component of the phosphoenolpyruvate:sugar phosphotransferase system, to the Escherichia coli lactose permease.	2002 Apr 30	11969416
The role of galactose, lactose, and galactose valency in the biorecognition of N-(2-hydroxypropyl)methacrylamide copolymers by human colon adenocarcinoma cells.	2002 Aug	12240936
Synthesis and evaluation of transition-state analogue inhibitors of alpha-1,3-fucosyltransferase.	2002 Aug 16	12203452
Expression of histo-blood group A antigen increases resistance to apoptosis and facilitates escape from immune control of rat colon carcinoma cells.	2002 Dec	12499407
Discordant expression of selectin ligands and sialyl Lewis x-related epitopes on murine myeloid cells.	2002 Dec 15	12393554
The alpha (1,3)-fucosyltransferase Fuc-TIV, but not Fuc-TVII, generates sialyl Lewis X-like epitopes preferentially on glycolipids.	2002 Dec 6	12359718
Two glycosylation alterations of mouse intestinal mucins due to infection caused by the parasite Nippostrongylus brasiliensis.	2002 Jan	12652082
The expression of human FUT1 in HT-29/M3 colon cancer cells instructs the glycosylation of MUC1 and MUC5AC apomucins.	2002 Jan	12652076
Transgenic pigs designed to express human CD59 and H-transferase to avoid humoral xenograft rejection.	2002 Jan	12005104
The cytosolic and transmembrane domains of the beta 1,6 N-acetylglucosaminyltransferase (C2GnT) function as a cis to medial/Golgi-targeting determinant.	2002 Jan	11825883
Fuc-TIX: a versatile alpha1,3-fucosyltransferase with a distinct acceptor- and site-specificity profile.	2002 Jun	12107078
Alpha1,4-fucosyltransferase activity: a significant function in the primate lineage has appeared twice independently.	2002 Jun	12032237
Detection of pigs resistant to post-weaning diarrhoea, oedema disease and porcine stress syndrome by allele-specific polymerase chain reaction.	2002 Jun	12030936
Increased thermosensitivity of mouse colorectal carcinoma cells transfected with human FUT1 gene.	2002 Jun 28	12175553
Enzymatic synthesis of oligosaccharide containing Le(x) unit by using partially purified chicken serum.	2002 Mar	12005061
Absorption of anti-blood group A antibodies on P-selectin glycoprotein ligand-1/immunoglobulin chimeras carrying blood group A determinants: core saccharide chain specificity of the Se and H gene encoded alpha1,2 fucosyltransferases in different host cells.	2002 Mar	11971861
Biosynthesis of the carbohydrate antigenic determinants, Globo H, blood group H, and Lewis b: a role for prostate cancer cell alpha1,2-L-fucosyltransferase.	2002 Mar	11971859
Fucosyltransferase VII-deficient mice with defective E-, P-, and L-selectin ligands show impaired CD4+ and CD8+ T cell migration into the skin, but normal extravasation into visceral organs.	2002 Mar 1	11859099
Isolation of a SIR-like gene, SIR-T8, that is overexpressed in thyroid carcinoma cell lines and tissues.	2002 Mar 18	11953824
Contribution of selectin ligands to eosinophil recruitment into the skin of patients with atopic dermatitis.	2002 May	11981814
Inhibitory effect of stevioside on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin.	2002 Nov	12419967
[Regulation by ovarian hormones of alpha 1,3-fucosyltransferase gene (FUT9) expression in human endometrium].	2002 Nov	12417923
Anthocyanin composition of the fruit of Coriaria myrtifolia L.	2002 Nov-Dec	12494755
Molecular genetic analysis of para-Bombay phenotypes in Chinese: a novel non-functional FUT1 allele is identified.	2002 Oct	12366770
Polymorphonuclear leukocytes from individuals carrying the G329A mutation in the alpha 1,3-fucosyltransferase VII gene (FUT7) roll on E- and P-selectins.	2002 Oct 1	12244194
Leukocyte rolling velocities and migration are optimized by cooperative L-selectin and intercellular adhesion molecule-1 functions.	2002 Oct 15	12370391
Molecular cloning and characterization of a novel alpha 1,2-fucosyltransferase (CE2FT-1) from Caenorhabditis elegans.	2002 Oct 18	12163507
A new geniculatoside from aerial parts of Euphorbia geniculata Linn.	2002 Sep	12369455
Enzyme kinetics, substitutable resources and competition: from biochemistry to frequency-dependent selection in lac.	2002 Sep	12242256
Pathophysiological contributions of fucosyltransferases in renal ischemia reperfusion injury.	2002 Sep 1	12193737
CCR6 colocalizes with CD18 and enhances adhesion to activated endothelial cells in CCR6-transduced Jurkat T cells.	2002 Sep 1	12193700
Distinct sulfation requirements of selectins disclosed using cells that support rolling mediated by all three selectins under shear flow. L-selectin prefers carbohydrate 6-sulfation totyrosine sulfation, whereas p-selectin does not.	2002 Sep 6	12068018
Expression levels of FUT6 gene transfected into human colon carcinoma cells switch two sialyl-Lewis X-related carbohydrate antigens with distinct properties in cell adhesion.	2003 Apr 11	12670495
Campylobacter jejuni binds intestinal H(O) antigen (Fuc alpha 1, 2Gal beta 1, 4GlcNAc), and fucosyloligosaccharides of human milk inhibit its binding and infection.	2003 Apr 18	12562767
Expression levels of H-type alpha(1,2)-fucosyltransferase gene and histo-blood group ABO gene corresponding to hematopoietic cell differentiation.	2003 Jan	12519432
Delayed rejection of porcine cartilage is averted by transgenic expression of alpha1,2-fucosyltransferase.	2003 Jan	12475900
N-terminal residues in murine P-selectin glycoprotein ligand-1 required for binding to murine P-selectin.	2003 Jan 15	12393631
C-terminal amino acids of Helicobacter pylori alpha1,3/4 fucosyltransferases determine type I and type II transfer.	2003 Jun 13	12676935
Immunobiological features of the galactoside lectin L-Lc isolated from the Argentine mistletoe Ligaria cuneifolia.	2003 Mar	12576206
Transactivation of the fucosyltransferase VII gene by human T-cell leukemia virus type 1 Tax through a variant cAMP-responsive element.	2003 May 1	12506041

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:05:42 UTC 2023` Edited by `admin` on `Fri Dec 15 15:05:42 UTC 2023`
Record UNII	X2RN3Q8DNE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GALACTOSE

Official Name

English

NSC-8102

Code

English

GALACTOSE [VANDF]

Common Name

English

(+)-GALACTOSE

Systematic Name

English

D-(+)-GALACTOSE

Systematic Name

English

GALACTOSE [NF]

Common Name

English

GALACTOSE [EP IMPURITY]

Common Name

English

D-GALACTOPYRANOSE

Systematic Name

English

GALACTOSE, D-

Systematic Name

English

GALACTOSE [II]

Common Name

English

LACTULOSE IMPURITY B [EP IMPURITY]

Common Name

English

D-GALACTOSE

Systematic Name

English

GALACTOSE [MART.]

Common Name

English

GALACTOSE, (+)-

Systematic Name

English

Galactose [WHO-DD]

Common Name

English

GALACTOSE [EP MONOGRAPH]

Common Name

English

CEREBROSE

Common Name

English

(3R,4S,5R,6R)-6-(HYDROXYMETHYL)TETRAHYDROPYRAN-2,3,4,5-TETROL

Systematic Name

English

BRAIN SUGAR

Common Name

English

GALACTOPYRANOSE, D-

Systematic Name

English

GALACTOSE [USP-RS]

Common Name

English

D-GALACTOSE [MI]

Common Name

English

GALACTOSE [INCI]

Common Name

English

GALACTOSE [USAN]

Common Name

English

Classification Tree Code System Code

LOINC

54085-6