13074-06-1

Basic information

• Product Name: 6-DEOXY-L-GALACTITOL
• Synonyms: 6-DEOXY-L-GALACTITOL;L-FUCITOL;1-Deoxy-D-galactitol;Rhodeitol
• CAS NO: 13074-06-1
• Molecular Formula: C₆H₁₄O₅
• Molecular Weight: 166.17
• Mol File: 13074-06-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 154-156 °C
• Boiling Point: 468°Cat760mmHg
• Flash Point: 244.3°C
• Appearance: /
• Density: 1.424g/cm³
• Vapor Pressure: 1.01E-10mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 13.58±0.20(Predicted)
• CAS DataBase Reference: 6-DEOXY-L-GALACTITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-DEOXY-L-GALACTITOL(13074-06-1)
• EPA Substance Registry System: 6-DEOXY-L-GALACTITOL(13074-06-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13074-06-1(Hazardous Substances Data)

Usage

Description

L-Fucitol is a reduced form of L-(–)-fucose . It has been used to determine the structure of E. coli and B. pallidus L-fucose isomerase.

InChI:InChI=1/C6H14O5/c1-3(8)5(10)6(11)4(9)2-7/h3-11H,2H2,1H3/t3-,4+,5+,6-/m0/s1

Upstream product

• 5139-39-9 S-ethyl-D-1-thio-galactitol 
• 59-23-4 D-Galactose 
• 2438-80-4 L-Fucose 
• 5463-33-2 D-galactose-diethyl-dithioacetal 
• 10231-84-2 (4-nitro-phenyl)-α-L-fucopyranoside 
• 488-28-8 hexane-1,2,3,4,5-pentaol 
• 6014-42-2 L-rhamnose 
• 210100-16-6 6-bromo-6-deoxy-L-galactonolactone 
• 1372946-80-9 methyl 6-bromo-6-deoxy-L-galactonate 
• 24286-28-0 (3S,4S,5R)-dihydro-3,4-dihydroxy-5-((1'S)-1'-hydroxyethyl)furan-2(3H)-one 
• 1668-08-2 L-galactono-1,4-lactone 
• 73-34-7 6-deoxy-L-galactose 
• 7699-34-5 6-deoxy-D-erythro-[2,5]hexodiulose 
• 7732-18-5 water 

Downstream Products

• 488-28-8 racemic rhodeitol 
• 42927-35-5 ((2S,3R)-2,2-dimethyl-5-((4'R,5'S)-2',2',5'-trimethyl-1',3'-dioxolan-4'-yl)-1,3-dioxolan-4-yl)methanol 
• 7226-60-0 1,2,3,4,5-penta-O-acetyl-L-fucitol 
• 86296-07-3 1-O-trityl-2.3.4.5-tetra-O-acetyl-L-fucitol 
• 42927-36-6 O²,O³;O⁴,O⁵-diisopropylidene-O⁶-(toluene-4-sulfonyl)-D-1-deoxy-galactitol 
• 123594-91-2 (6S)-1-deoxy-D-galactitol 6-(9-anthroate) 2,3,4,5-tetra-p-methoxycinnamate 
• 170452-37-6 2,3,4,5-tetra-O-benzoyl-L-fucitol 
• 170452-38-7 2,3,4,5-tetra-O-benzoyl-aldehydo-L-fucose 

Relevant articles and documents

Designer α1,6-Fucosidase Mutants Enable Direct Core Fucosylation of Intact N-Glycopeptides and N-Glycoproteins

Core fucosylation of N-glycoproteins plays a crucial role in modulating the biological functions of glycoproteins. Yet, the synthesis of structurally well-defined, core-fucosylated glycoproteins remains a challenging task due to the complexity in multistep chemical synthesis or the inability of the biosynthetic α1,6-fucosyltransferase (FUT8) to directly fucosylate full-size mature N-glycans in a chemoenzymatic approach. We report in this paper the design and generation of potential α1,6-fucosynthase and fucoligase for direct core fucosylation of intact N-glycoproteins. We found that mutation at the nucleophilic residue (D200) did not provide a typical glycosynthase from this bacterial enzyme, but several mutants with mutation at the general acid/base residue E274 of the Lactobacillus casei α1,6-fucosidase, including E274A, E274S, and E274G, acted as efficient glycoligases that could fucosylate a wide variety of complex N-glycopeptides and intact glycoproteins by using α-fucosyl fluoride as a simple donor substrate. Studies on the substrate specificity revealed that the α1,6-fucosidase mutants could introduce an α1,6-fucose moiety specifically at the Asn-linked GlcNAc moiety not only to GlcNAc-peptide but also to high-mannose and complex-type N-glycans in the context of N-glycopeptides, N-glycoproteins, and intact antibodies. This discovery opens a new avenue to a wide variety of homogeneous, core-fucosylated N-glycopeptides and N-glycoproteins that are hitherto difficult to obtain for structural and functional studies.

Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-d-tagatose from l-fucose and of 6-deoxy-d-tagatose from d-fucose using Enterobacter agglomerans strain 221e

1-Deoxy-d-tagatose was produced by the hydrogenation of 6-deoxy-l-galactose (l-fucose) to l-fucitol followed by oxidation with Enterobacter agglomerans 221e; a similar sequence on d-fucose afforded 6-deoxy-d-tagatose. Thus, the polylol dehydrogenase recognizes the d-galacto-configuration of both d-fucitol and l-fucitol. The procedures were conducted in water and show the power of green, environmentally friendly biotechnology in the preparation of new monosaccharides with a potential for novel bioactive properties. 6-Deoxy-d-tagatose was also synthesized from d-tagatose via the efficient formation of 1,2:3,4-di-O-isopropylidene-α-d-tagatofuranose; a difficult final removal of protecting groups by acid makes the biotechnological route more attractive.

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Effect of carbon chain length on catalytic C–O bond cleavage of polyols over Rh-ReOx/ZrO2 in aqueous phase

Production of linear deoxygenated C4 (butanetriols, -diols, and butanols), C5 (pentanetetraols, -triols, -diols, and pentanols), and C6 products (hexanepentaols, -tetraols, -triols, -diols, and hexanols) is achievable by hydrogenolysis of erythritol, xylitol, and sorbitol over supported-bimetallic Rh-ReOx (Re/Rh molar ratio 0.5) catalyst, respectively. After validation of the analytical methodology, the effect of some reaction parameters was studied. In addition to C–O bond cleavage by hydrogenolysis, these polyols can undergo parallel reactions such as epimerization, cyclic dehydration, and C–C bond cleavage. The time courses of each family of linear deoxygenated C4, C5, and C6 products confirmed that the sequence of appearance of the different categories of deoxygenated products followed a multiple sequential deoxygenation pathway. The highest selectivity to a mixture of linear deoxygenated C4, C5, and C6 products at 80percent conversion was favoured under high pressure in the presence of 3.7wt.percentRh-3.5wt.percentReOx/ZrO2 catalysts (54–71percent under 80 bar) at 200 °C.