Lactosillan

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Category Others
Catalog number BBF-02241
CAS 83712-86-1
Molecular Weight 821.77
Molecular Formula C32H55NO23

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Description

It is produced by the strain of Alcaligenes latus G66A. Latosillan is a cell differentiation inducer that can differentiate myeloid leukemia cells into macrophages.

Specification

Synonyms Latosillan
IUPAC Name N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4R,5R,6S)-6-[(2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-[(2S,3R,4S,5R,6S)-4,5,6-trihydroxy-2-methyloxan-3-yl]oxyoxan-3-yl]oxy-4-hydroxy-2-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Canonical SMILES CC1C(C(C(C(O1)O)O)O)OC2C(C(C(C(O2)C)OC3C(C(C(C(O3)C)OC4C(C(C(C(O4)CO)O)O)NC(=O)C)O)OC5C(C(C(C(O5)CO)O)O)O)O)O
InChI InChI=1S/C32H55NO23/c1-7-24(18(41)20(43)28(47)48-7)54-30-22(45)19(42)25(8(2)49-30)55-32-27(56-31-21(44)17(40)15(38)12(6-35)52-31)23(46)26(9(3)50-32)53-29-13(33-10(4)36)16(39)14(37)11(5-34)51-29/h7-9,11-32,34-35,37-47H,5-6H2,1-4H3,(H,33,36)/t7-,8-,9-,11+,12+,13+,14+,15+,16+,17-,18-,19-,20+,21+,22+,23+,24-,25-,26-,27+,28-,29-,30-,31-,32-/m0/s1
InChI Key LGNAXCRAGJPZAU-LVDOCHHTSA-N

Properties

Appearance White Powder
Solubility Soluble in Sodium hydroxide

Reference Reading

1. Synthesis of the pentasaccharide repeating unit of lactosillan [correction of latosillan]
Yuxia Hua, Junjun Xiao, Yingshen Huang, Yuguo Du Carbohydr Res. 2006 Feb 6;341(2):191-7. doi: 10.1016/j.carres.2005.11.007. Epub 2005 Dec 5.
A pentasaccharide, beta-D-Man-(1-->2)-[beta-D-GlcNAc-(1-->4)]-alpha-L-Rha-(1-->4)-alpha-L-Rha-(1-->4)-alpha-L-Rha-1-OC8H17, representing the repeating unit of latosillan, was convergently synthesized from the building blocks, ethyl 2,3-O-isopropylidene-1-thio-alpha-l-rhamnopyranoside, 2-O-acetyl-3,4,6-tri-O-benzyl-beta-d-glucopyranosyl trichloroacetimidate, and 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-d-glucopyranosyl trichloroacetimidate under standard glycosylation conditions. The target pentasaccharide showed acceptable differentiation-inducing activity on HL-60 cell lines at the dosages of 10-50 microg/mL.

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