Hydroxymethylbilane: Difference between revisions

{{Short description|Intermediate in the synthesis of porphyrins}}

| verifiedrevid = 443862987

| ImageSize=

| IUPACName=3,3′,3′′,3′′′-[3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)-5,10,15,22,23,24-hexahydro-21''H''-biline-2,7,12,17-tetrayl]tetrapropanoic acid

| SystematicName=3,3′,3′′,3′′′-[1⁴,3³,5³,7³-Tetrakis(carboxymethyl)-1⁵-(hydroxymethyl)-1¹''H'',3¹''H'',5¹''H'',7¹''H''-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-1³,3⁴,5⁴,7⁴-tetrayl]tetrapropanoic acid

| OtherNames=

|Section1={{Chembox Identifiers

| Beilstein = 1209089

| CASNo_Ref = {{cascite|changed|CAS}}

| CASNo=71861-60-4

| PubChem=788

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 767

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 16645

| KEGG = C01024

| SMILES = O=C(O)Cc1c(c[nH]c1Cc2c(c(c([nH]2)Cc3[nH]c(c(c3CCC(=O)O)CC(=O)O)Cc4c(c(c([nH]4)CO)CC(=O)O)CCC(=O)O)CC(=O)O)CCC(=O)O)CCC(=O)O

| InChI = 1/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)

| InChIKey = WDFJYRZCZIUBPR-UHFFFAOYAI

| MeSHName=hydroxymethylbilane

|Section2={{Chembox Properties

| Formula=C₄₀H₄₆N₄O₁₇

| MolarMass=854.81 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

'''Hydroxymethylbilane''', also known as '''preuroporphyrinogen''', is an [[organic compound]] that occurs in living organisms during the synthesis of [[porphyrin]]s, a group of critical substances that include [[haemoglobin]], [[myoglobin]], and [[chlorophyll]]. The name is often abbreviated as '''HMB'''.

== Structure ==

The compound is a substituted [[bilane]], a chain of four [[pyrrole]] rings interconnected by [[methylene bridge]]s {{chem2|\sCH2\s}}. The chain starts with a [[hydroxymethyl]] group {{chem2|\sCH2\sOH}} and ends with an [[hydrogen]], in place of the respective methylene bridges. The other two carbon atoms of each pyrrole cycle are connected to an [[acetic acid]] group {{chem2|\sCH2\sCOOH}} and a [[propionic acid]] group {{chem2|\sCH2\sCH2\sCOOH}}, in that order.<ref name="Hemes">{{cite encyclopedia|chapter=Hemes in Biology|author=Paul R. Ortiz de Montellano|year=2008|encyclopedia=Wiley Encyclopedia of Chemical Biology|doi=10.1002/9780470048672.wecb221|publisher=John Wiley & Sons|isbn=978-0470048672}}</ref>

== Metabolism ==

HMB is generated from four molecules of [[porphobilinogen]] by the [[enzyme]] [[porphobilinogen deaminase]]:<ref name=":0">{{Cite book |last=Voet |first=Donald |title=Biochemistry |last2=Voet |first2=Judith G. |date=2011 |publisher=Wiley |isbn=978-0-470-57095-1 |edition=4. |location=Hoboken, NJ}}</ref>

[[File:Pre-uroporphyrinogen-synthesis-from-porphobilinogen.png|center|420px|alt=Biosynthesis of pre-uroporphyrinogen from porphobilinogen]]

The enzyme [[uroporphyrinogen III synthase]] closes the chain to form [[uroporphyrinogen III]]:<ref name=":0" />

[[File:Uroporphyrinogen-III-synthesis-from-pre-uroporphyrinogen.png|center|frameless|564x564px]]

Uroporphyrinogen III is a [[porphyrinogen]], which is a class of compounds with the [[hexahydroporphine]] [[macrocycle]]. In the absence of the enzyme, the compound undergoes spontaneous cyclization and becomes [[uroporphyrinogen I]].<ref name="Hemes2">{{cite encyclopedia |year=2008 |encyclopedia=Wiley Encyclopedia of Chemical Biology |publisher=John Wiley & Sons |doi=10.1002/9780470048672.wecb221 |isbn=978-0470048672 |chapter=Hemes in Biology |author=Paul R. Ortiz de Montellano}}</ref><ref name="sassa">{{cite journal |last1=Sassa |first1=S. |last2=Kappas |first2=A. |year=2000 |title=Molecular aspects of the inherited porphyrias |journal=Journal of Internal Medicine |volume=247 |issue=2 |pages=169–178 |doi=10.1046/j.1365-2796.2000.00618.x |pmid=10692079 |s2cid=36820694|doi-access=free }}</ref>

==References==

{{reflist}}

{{Heme metabolism intermediates}}

[[Category:Tetrapyrroles]]

[[Category:Carboxylic acids]]