Deoxyadenosine monophosphate

Deoxyadenosine monophosphate (dAMP), also known as deoxyadenylic acid or deoxyadenylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleotide adenosine monophosphate (AMP), in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been reduced to just a hydrogen atom (hence the "deoxy-" part of the name). Deoxyadenosine monophosphate is abbreviated dAMP. It is a monomer used in DNA.

Deoxyadenosine monophosphate

Names
IUPAC name 2′-Deoxyadenylic acid
Systematic IUPAC name [(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Identifiers
CAS Number	653-63-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17713 Y
ChemSpider	12079 Y
ECHA InfoCard	100.010.459
IUPHAR/BPS	5120
MeSH	Deoxyadenosine+monophosphate
PubChem CID	621
UNII	VFR8I97ORM Y
CompTox Dashboard (EPA)	DTXSID901034859
InChI InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 Y Key: KHWCHTKSEGGWEX-RRKCRQDMSA-N Y InChI=1/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 Key: KHWCHTKSEGGWEX-RRKCRQDMBS
SMILES c1nc(c2c(n1)n(cn2)[C@H]3C[C@@H]([C@H](O3)COP(=O)(O)O)O)N
Properties
Chemical formula	C10H14N5O6P
Molar mass	331.222 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Chemical Properties

The overall structure of dAMP is shaped largely by how its parts interact with each other. In particular, the adenine base and the phosphate group can form hydrogen bond interactions. The distance between the atoms involved in these bonds helps shape the overall conformation of dAMP. The character of these interactions shifts with the molecule’s charge state. When the molecule gains or loses charge, it causes the spacing between the atoms to fluctuate.^[1] Increasing the negative charge, tends to draw the atoms closer together, causing the strength of the hydrogen bond to increase as well. ^[1] Protonation of the adenine increases the strength of the hydrogen bonds. The presence of water molecules can also stabilize the structure by forming additional hydrogen bonds with the phosphate group and the adenine base.^[2]

See also

• Nucleic acid
• DNA metabolism
• Cofactor
• Guanosine
• Cyclic AMP (cAMP)
• ATP