bialaphos

{{chembox

| Watchedfields = changed

| verifiedrevid =

| Reference =

| ImageFile = Bialaphos.svg

| SystematicName = (2S)-2-[(2S)-2-{(2S)-2-Amino-4-[hydroxy(methylphosphonoyl)]butanamido}propanamido]propanoic acid

| OtherNames = L-Alanyl-L-alanyl-phosphinothricin

|Section1={{Chembox Identifiers

| KEGG_Ref = {{keggcite|correct|kegg}}=

| KEGG =

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 35597-43-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7488PCM6I2

| PubChem = 5462314

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

| ChemSpiderID = 4575372

| SMILES = O=C(O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CCP(=O)(O)C)C)C

| InChI = 1/C11H22N3O6P/c1-6(9(15)14-7(2)11(17)18)13-10(16)8(12)4-5-21(3,19)20/h6-8H,4-5,12H2,1-3H3,(H,13,16)(H,14,15)(H,17,18)(H,19,20)/t6-,7-,8-/m0/s1

| InChIKey = GINJFDRNADDBIN-FXQIFTODBR

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H22N3O6P/c1-6(9(15)14-7(2)11(17)18)13-10(16)8(12)4-5-21(3,19)20/h6-8H,4-5,12H2,1-3H3,(H,13,16)(H,14,15)(H,17,18)(H,19,20)/t6-,7-,8-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GINJFDRNADDBIN-FXQIFTODSA-N

}}

|Section2={{Chembox Properties

| C=11 | H=22 | N=3 | O=6 | P=1

| Appearance =

| Density = 1.33 g/mL

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|Section3={{Chembox Hazards

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Bialaphos is a natural herbicide produced by the bacteria Streptomyces hygroscopicus{{cite journal | doi = 10.1007/BF02428031 | title = The bialaphos biosynthetic genes of Streptomyces hygroscopicus: Molecular cloning and characterization of the gene cluster | year = 1986 | last1 = Murakami | first1 = Takeshi | last2 = Anzai | first2 = Hiroyuki | last3 = Imai | first3 = Satoshi | last4 = Satoh | first4 = Atsuyuki | last5 = Nagaoka | first5 = Kozo | last6 = Thompson | first6 = Charles J. | journal = MGG Molecular & General Genetics | volume = 205 | pages = 42–53| s2cid = 32983239 }} and Streptomyces viridochromogenes. It is also known by the ISO common name bilanafos.{{cite web |url=http://www.bcpcpesticidecompendium.org/bilanafos.html |title=Compendium of Pesticide Common Names: Bilanafos |publisher=BCPC |access-date=2024-05-07}} Bialaphos is a protoxin and nontoxic as is. When it is metabolized by a plant, the glutamic acid analog glufosinate is released which inhibits glutamine synthetase. This results in the accumulation of ammonium and disruption of primary metabolism.{{cite journal | doi = 10.3390/toxins3081038 | title = Modes of Action of Microbially-Produced Phytotoxins | year = 2011 | last1 = Duke | first1 = Stephen O. | last2 = Dayan | first2 = Franck E. | journal = Toxins (Basel) | volume = 3 | issue = 8 | pages = 1038–1064| pmid = 22069756 | pmc = 3202864 | citeseerx = 10.1.1.288.3457 | doi-access = free }}

Bialaphos is made up of two alanine residues and glufosinate, and is commonly used as a selection marker in plants. Resistance plasmids include pGreenII 0229 and pGreenII 0229 62-SK. pGreenII 0229 is derived from pGreenII 0000, a nos-{{abbr|bar|Bialaphos resistance gene}} cassette has been inserted into the HpaI site of the left border, providing resistance to bialaphos or phosphinothricin during plant transformation selection. pGreenII 0229 62-SK is derived from pGreenII 0229, the LacZ blue/white cloning selection has been replaced with a 35S-MCS-CaMV cassette that allows the insertion of a gene of interest into a 35S overexpression cassette.{{cite web|title=Bialaphos as plant gene selector|url=http://www.toku-e.com/Upload/Products/PDS/20120618004028.pdf|accessdate=20 June 2012|archive-url=https://web.archive.org/web/20141021233510/http://www.toku-e.com/Upload/Products/PDS/20120618004028.pdf|archive-date=21 October 2014|url-status=dead}}