Glucolipsin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01262 |
| CAS | 222613-92-5 |
| Molecular Weight | 917.25 |
| Molecular Formula | C50H92O14 |
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Description
It is produced by the strain of Streptomyces purpurogeniscleroticus WC 71634, Nocardia vaccinii WC 65712. It is a glucokinase activator. It can reactivate the glucokinase inhibited by FAC with RC50 of 5.4 μmol/L.
Specification
| IUPAC Name | (1R,8S,9R,10R,11S,12S,19R,20S,21S,22R)-9,10,11,20,21,22-hexahydroxy-4,15-dimethyl-3,14-bis(13-methyltetradecyl)-2,6,13,17,23,24-hexaoxatricyclo[17.3.1.18,12]tetracosane-5,16-dione |
| Canonical SMILES | CC1C(OC2C(C(C(C(O2)COC(=O)C(C(OC3C(C(C(C(O3)COC1=O)O)O)O)CCCCCCCCCCCCC(C)C)C)O)O)O)CCCCCCCCCCCCC(C)C |
| InChI | InChI=1S/C50H92O14/c1-33(2)27-23-19-15-11-7-9-13-17-21-25-29-37-35(5)47(57)59-31-40-42(52)44(54)46(56)50(64-40)62-38(30-26-22-18-14-10-8-12-16-20-24-28-34(3)4)36(6)48(58)60-32-39-41(51)43(53)45(55)49(61-37)63-39/h33-46,49-56H,7-32H2,1-6H3/t35?,36?,37?,38?,39-,40+,41-,42+,43+,44-,45-,46+,49-,50+ |
| InChI Key | TURVNPRDJNOSQM-CETMAINBSA-N |
Properties
| Appearance | White Powder |
| Solubility | Soluble in Methanol |
Reference Reading
1. Glucolipsin A and B, two new glucokinase activators produced by Streptomyces purpurogeniscleroticus and Nocardia vaccinii
J Qian-Cutrone, T Ueki, S Huang, K A Mookhtiar, R Ezekiel, S S Kalinowski, K S Brown, J Golik, S Lowe, D M Pirnik, R Hugill, J A Veitch, S E Klohr, J L Whitney, S P Manly J Antibiot (Tokyo). 1999 Mar;52(3):245-55. doi: 10.7164/antibiotics.52.245.
During the screening of the natural products for their ability to increase the activity of glucokinase by relieving inhibition by long chain fatty acyl CoA esters (FAC), two novel compounds, glucolipsin A (1) and B (2) were isolated from the butanol extracts of Streptomyces purpurogeniscleroticus WC71634 and Nocardia vaccinii WC65712, respectively. The structures of these two compounds were established by spectroscopic methods and chemical degradation. Glucolipsin A (1) and B (2) relieved the inhibition of glucokinase by FAC with RC50 values of 5.4 and 4.6 microM.
2. A concise synthesis of the fully functional lactide core of cycloviracin B with implications for the structural assignment of related glycolipids
Alois Fürstner, Martin Albert, Jacek Mlynarski, Maribel Matheu J Am Chem Soc. 2002 Feb 20;124(7):1168-9. doi: 10.1021/ja0175791.
The absolute stereochemistry at the site of attachment of the fatty acid residues to the lactide core of the glycolipids cycloviracin B1 (1) and glucolipsin A (13) has been elucidated as (3R,3'R) by comparison of their 13C NMR data with those of the three possible, differently configured core structures 9, 12, and 14. Moreover, a careful analysis of this set of NMR data allows us to conclude that the structures previously proposed for a seemingly closely related class of antivirally active compounds, i.e., the fattiviracin family, need revision. The key step en route to the symmetrical dilactones 9 and 12 consists of a highly efficient cyclodimerization process which exploits the template effect exerted by potassium cations on the hydroxy acid cyclization precursor. The latter is obtained in excellent overall yield by a sequence involving ring-opening Claisen condensation of pentadecanolide to form the functionalized beta-ketoester 4, asymmetric hydrogenation catalyzed by [(BINAP)RuCl2]2.NEt3, and a beta-selective glycosylation reaction using trichloroacetimidate 6. The unsymmetrical dilactone 14, in contrast, is prepared by a stepwise approach based on a Yamaguchi lactonization as the means to close the macrocyclic ring.
3. Structure assignment, total synthesis, and evaluation of the phosphatase modulating activity of glucolipsin A
Alois Fürstner, Juliana Ruiz-Caro, Heino Prinz, Herbert Waldmann J Org Chem. 2004 Jan 23;69(2):459-67. doi: 10.1021/jo035079f.
The previously unknown stereostructure of glucolipsin A (1), a complex glycolipid endowed with glucokinase-activating properties, was unambiguously elucidated as (2R,2'R,3S,3'S) by comparison of its spectroscopic and analytical data with those of all conceivable C(2)-symmetric stereoisomers. This set of macrodiolides was prepared by a sequence comprising auxiliary guided aldol reactions, glycosidation of the resulting beta-hydroxy acid derivatives with trichloroacetimidate 7, followed by hydrolytic cleavage of the auxiliaries used. The hydroxy acids thus formed were subjected to a macrodilactonization reaction mediated by 2-chloro-1,3-dimethylimidazolinium chloride (22) as the activating agent; this transformation is highly productive only in the presence of admixed potassium cations which likely serve as templates to preorganize two substrate molecules in a favorable head-to-tail arrangement. Glucolipsin and analogues were subjected to enzymatic assays that revealed that glycoconjugates of this type effectively inhibit the activity of the dual specific phosphatase Cdc25A with IC(50) values in the low micromolar range, while being hardly active against the tyrosine phosphatase PTP1B in vitro. This activity profile was compared to that of other glycolipids previously prepared in this laboratory, including cycloviracin B(1) (2), caloporoside (38), woodrosin I (39), sophorolipid lactone (40), and tricolorin G (41).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
