Alloisoleucine
{{Chembox
| ImageFile = L-alloisoleucine.svg
| ImageSize =
| ImageAlt =
| IUPACName =
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 1509-35-8
| index_label = L-enantiomer
| CASNo1 = 1509-34-9
| index1_label = D enantiomer
| CASNo2 = 3107-04-8
| index2_label = racemic
| Beilstein = 1721791
| ChEBI = 43433
| ChEBI1 = 20899
| ChEMBL = 56053
| ChemSpiderID = 89698
| ChemSpiderID1 = 85019
| DrugBank = DB01739
| EC_number = 216-142-3
| EC_number2 = 207-139-8
| PubChem = 99288
| PubChem1 = 94206
| UNII = 6RNR8XN7S2
| UNII2 = 05T3WT3PJ1
| StdInChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5+/m1/s1
| StdInChIKey = AGPKZVBTJJNPAG-UHNVWZDZSA-N
| InChI1=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5+/m0/s1
| InChIKey1 = AGPKZVBTJJNPAG-CRCLSJGQSA-N
| SMILES = CC[C@@H](C)[C@@H](C(=O)O)N
| SMILES1 =CC[C@H](C)[C@H](C(=O)O)N
| SMILES2 =CCC(C)C(C(=O)O)N
}}
|Section2={{Chembox Properties
| Formula =
| MolarMass =
| Appearance = white solid
| Density =
| MeltingPtC = 285
| MeltingPt_notes =
| BoilingPt =
| BoilingPt_notes =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Alloisoleucine is an amino acid with the formula {{chem2|CH3CH2CH(CH3)CH(NH2)CO2H}}. It exists as two enantiomers, of which the L derivative occurs naturally. L-Alloisoleucine occurs in healthy serum in only trace amounts, except for individuals suffering from maple syrup urine disease.{{cite journal |doi=10.1203/00006450-200002000-00020 |title=Formation of L-Alloisoleucine in Vivo : An L-[13C]Isoleucine Study in Man |year=2000 |last1=Schadewaldt |first1=Peter |last2=Bodner-Leidecker |first2=Annette |last3=Hammen |first3=Hans-Werner |last4=Wendel |first4=Udo |journal=Pediatric Research |volume=47 |issue=2 |pages=271–277 |pmid=10674358 |s2cid=530588 |doi-access=free }}
Structure
Together with valine, leucine, and isoleucine, alloisoleucine is classified as a branched-chain amino acid (BCAA). It is the rarest of the four.
L-Alloisoleucine is a diastereomer of the proteogenic amino acid L-isoleucine. The stereochemistry of the isobutyl group differs for L-alloisoleucine and L-isoleucine.
| class="wikitable centered" style="text-align:center" |
| 200px 200px |
| {{sm|l}}-isoleucine (2S,3S) and {{sm|d}}-isoleucine (2R,3R) |
| 200px 200px |
| {{sm|l}}-alloisoleucine (2S,3R) and {{sm|d}}-alloisoleucine (2R,3S) |
Role in biosynthesis
L-allo-isoleucine is a precursor to coronamic acid, which is a constituent of the phytotoxin coronatine, produced by Pseudomonas syringae.{{Cite journal |last1=Vaillancourt |first1=Frédéric H. |last2=Yeh |first2=Ellen |last3=Vosburg |first3=David A. |last4=O'Connor |first4=Sarah E. |last5=Walsh |first5=Christopher T. |date=August 2005 |title=Cryptic chlorination by a non-haem iron enzyme during cyclopropyl amino acid biosynthesis |url=https://www.nature.com/articles/nature03797 |journal=Nature |language=en |volume=436 |issue=7054 |pages=1191–1194 |doi=10.1038/nature03797 |pmid=16121186 |bibcode=2005Natur.436.1191V |s2cid=4428247 |issn=1476-4687|url-access=subscription }}