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03418

Sigma-Aldrich

L-Rhamnono-1,5-lactone

≥98% (TLC)

Synonym(s):

(3R,4R,5R,6S)-3,4,5-Trihydroxy-6-methyl-3H-4,5,6-trihydropyran-2-one, 6-Deoxy-L-mannonic acid δ-lactone, L-Rhamnoic 1,5-lactone, L-Rhamnonic acid δ-lactone

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About This Item

Empirical Formula (Hill Notation):
C6H10O5
CAS Number:
69992-12-7
Molecular Weight:
162.14
Beilstein/REAXYS Number:
82519
MDL number:
MFCD28100798
UNSPSC Code:
12352204
PubChem Substance ID:
329747627
NACRES:
NA.32

assay

≥98% (TLC)

form

powder

optical activity

[α]/D -95±5°, c = 3 in H2O

suitability

conforms to structure for Infrared spectrum

storage temp.

2-8°C

SMILES string

O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)OC1=O

InChI

1S/C6H10O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-5,7-9H,1H3/t2-,3-,4+,5+/m0/s1

InChI key

ZVAHHEYPLKVJSO-QMKXCQHVSA-N

Biochem/physiol Actions

Metabolite of L-rhamnose catabolic pathway.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
STBD8702V

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β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose).
Varela, O.J., et al.
Carbohydrate Research, 70, 27-35 (1979)
Torsten Haack et al.
The Journal of organic chemistry, 70(19), 7592-7604 (2005-09-10)
[reaction: see text] Two formal total syntheses of the (-)-salicylihalamides, based on chiral pool approaches, are reported. D-glucose and L-rhamnose were used to prepare advanced intermediates 23 and 54, which can be converted in three or four steps, respectively, to
β-Elimination in aldonolactones. the conversion of l-rhamnono-1-5-lactone into 3-benzoyloxy-6-methylpyran-2-one
Varela, O.J., et al.
Carbohydrate Research, 79, 219-224 (1980)
Merlin Eric Hobbs et al.
Biochemistry, 52(1), 239-253 (2012-12-12)
A member of the amidohydrolase superfamily, BmulJ_04915 from Burkholderia multivorans, of unknown function was determined to hydrolyze a series of sugar lactones: L-fucono-1,4-lactone, D-arabino-1,4-lactone, L-xylono-1,4-lactone, D-lyxono-1,4-lactone, and L-galactono-1,4-lactone. The highest activity was shown for L-fucono-1,4-lactone with a k(cat) value of
Andreas Reinhardt et al.
Molecular microbiology, 111(4), 1093-1108 (2019-02-02)
The halophilic archaeon Haloferax volcanii utilizes l-rhamnose as a sole carbon and energy source. It is shown that l-rhamnose is taken up by an ABC transporter and is oxidatively degraded to pyruvate and l-lactate via the diketo-hydrolase pathway. The genes

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