AHCYS – S-Adenosyl-L-homocysteine

Name
WID AHCYS View in model
Name S-Adenosyl-L-homocysteine View in model
Traditional name 2-aminio-4-({[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoate
IUPAC name 4-({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)-2-azaniumylbutanoate
Cross references ChEBI: 25246222, PubChem: 3323, CAS: 979-92-0, BioCyc: ADENOSYL-HOMO-CYS, BiGG: ahcys, ... 4 more
 
Structure
Empirical formula (pH 7.5) H20C14N6O5S1
SMILES (pH 7.5) NC1=NC=NC2=C1N=CN2C1OC(CSCCC([NH3+])C([O-])=O)C(O)C1O
Charge (pH 7.5) 0
Is hydrophobic False View in model
Molecular weight (Da) 384.41 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)		 316.87
ΔfG'o (pH 7.5, 25C, I = 0; kJ mol‑1) 540.70
pI 7.32
logP -4.17
logD (pH 7.5) -4.16
 
Function
Reaction participant View in model
 
Comments
Comments Byproduct of DNA, RNA, and protein methylation by S-Adenosyl-L-methionine (AMET). Added to media to allow phosphonate uptake and fit observed phosphate transporter (MG_410-2) gene essentiality. Typical phosphonate concetrations: Brine: 0.1-10 mg/L [PUB_0769] Fresh water: 0.02 mg/L [PUB_0769] Tetrahymena: 0-10 mM [PUB_0770] Penicillium notatum media sole phosphorous source: 1 mM [PUB_0771] E. coli medium organic phosphate source: 2 mM [PUB_0772] Microbial growth media: 4 mM [PUB_0773]
References

  1. Bujacz B, Wieczorek P, Krzysko-Lupicka T, Golab Z, Lejczak B, Kavfarski P. Organophosphonate Utilization by the Wild-Type Strain of Penicillium notatum. Appl Environ Microbiol 61, 2905-10 (1995). WholeCell: PUB_0771, PubMed: 16535094

  2. Elashvili I, Defrank JJ, Culotta VC. phnE and glpT genes enhance utilization of organophosphates in Escherichia coli K-12. Appl Environ Microbiol 64, 2601-8 (1998). WholeCell: PUB_0772, PubMed: 9647836

  3. Kan AT, Varughese K, Tomson MB. Determination of Low Concentrations of Phosphonate in Brines. Society of petroleum engineers 21006, 109-114 (1991). WholeCell: PUB_0769, URL: http://www2.dupont.com/Powder/en_US/assets/downloads/literature/25_Determination_of_Low_Concentration_of_Phosphonate_in_Brines.pdf

  4. Klimek-Ochab M, Obojska A, Picco AM, Lejczak B. Isolation and characterization of two new microbial strains capable of degradation of the naturally occurring organophosphonate - ciliatine. Biodegradation 18, 223-31 (2007). WholeCell: PUB_0773, PubMed: 16758270

  5. Smith JD, O'Malley MA. Control of phosphonic acid and phosphonolipid synthesis in Tetrahymena. Biochim Biophys Acta 528, 394-8 (1978). WholeCell: PUB_0770, PubMed: 416849
 
Metadata
Created 2012-10-01 15:06:49
Last updated 2012-10-01 15:11:53