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[ CAS No. 27821-45-0 ] {[proInfo.proName]}

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Chemical Structure| 27821-45-0
Chemical Structure| 27821-45-0
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Product Citations

Product Citations

Moore, Maxwell J. ; Qin, Pengjin ; Keith, D. Jamin , et al. DOI: PubMed ID:

Abstract: Modifications to the enzymic glycosylation of vancomycin and its residue 4 thioamide analog are detailed that significantly reduce the enzyme loading and amount of glycosyl donor needed for each glycosylation reaction, provide a streamlined synthesis and replacement for the synthetic UDP-vancosamine glycosyl donor to improve both access and storage stability, and permit a single-pot, two-step conversion of the aglycons to the fully glycosylated synthetic glycopeptides now conducted at higher concentrations The improvements are exemplified with the two-step, one-pot glycosylation of [Ψ[C(=S)NH]Tpg4]vancomycin aglycon (92%) conducted on a 400 mg scale (2 mg-1 g scales) and vancomycin aglycon itself (5 mg scale, 84%).

Keywords: Vancomycin ; Vancomycin analogues ; Enzymatic glycosylation

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Product Details of [ 27821-45-0 ]

CAS No. :27821-45-0 MDL No. :MFCD00084679
Formula : C9H12N2Na2O12P2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 448.12 Pubchem ID :-
Synonyms :
UDP disodium salt
Chemical Name :Sodium ((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl hydrogen diphosphate

Calculated chemistry of [ 27821-45-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.56
Num. rotatable bonds : 6
Num. H-bond acceptors : 12.0
Num. H-bond donors : 4.0
Molar Refractivity : 73.03
TPSA : 243.12 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -12.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : -41.2
Log Po/w (XLOGP3) : -4.72
Log Po/w (WLOGP) : -2.07
Log Po/w (MLOGP) : -4.52
Log Po/w (SILICOS-IT) : -3.58
Consensus Log Po/w : -11.22

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.11

Water Solubility

Log S (ESOL) : 0.59
Solubility : 1730.0 mg/ml ; 3.86 mol/l
Class : Highly soluble
Log S (Ali) : 0.24
Solubility : 781.0 mg/ml ; 1.74 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 2.46
Solubility : 131000.0 mg/ml ; 292.0 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.54

Safety of [ 27821-45-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:
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