Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Polylysine: Difference between pages

| Watchedfields = changed

| verifiedrevid = 464209954

| Name = ε-Polylysine

| ImageFile = polylysine.png

| ImageName = Skeletal formula of ε-polylysine

| IUPACName = Poly[imino[(2''S'')-2-amino-1-oxo-1,6-hexanediyl

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 25104-18-1

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

| UNII = 0A1V8JTU2M

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = none

|Section2={{Chembox Properties

| Formula = (C₆H₁₂N₂O)_n

| MolarMass = variable<br>4700 g/mol <small>(degree of polymerization = 30)</small>

| MeltingPtC = 142.2

| Solubility = Soluble

| pKb = 5

'''Polylysine''' refers to several types of [[lysine]] [[homopolymer]]s, which may differ from each other in terms of stereochemistry (D/L; the L form is natural and usually assumed) and link position (α/ε). Of these types, only ε-poly-L-lysine is produced naturally.

==Chemical structure==

{{missing information|section|DL mixed (alpha)-poly-DL-lysine — seems to have some use involving copper|date=October 2022}}

The precursor amino acid lysine contains two [[amino group]]s, one at the [[Alpha and beta carbon#Proteins and amino acids|α-carbon]] and one at the ε-carbon. Either can be the location of [[polymerization]], resulting in α-polylysine or ε-polylysine. Polylysine is a homopolypeptide belonging to the group of [[cationic]] [[polymer]]s: at [[pH]] 7, polylysine contains a positively charged [[hydrophilic]] amino group.

[[File:Alpha-Polylysine.png|left|thumb|upright=0.5|Structure of α-polylysine]]

α-Polylysine is a synthetic polymer, which can be composed of either <small>L</small>-lysine or <small>D</small>-lysine. "L" and "D" refer to the [[chirality]] at lysine's central carbon. This results in poly-<small>L</small>-lysine (PLL) and poly-<small>D</small>-lysine (PDL) respectively.<ref>Sitterley, G. (2008). Poly-l-lysine cell attachment protocol. BioFiles, 3(8), 12.</ref>

ε-Polylysine (ε-poly-<small>L</small>-lysine, EPL) is typically produced as a homopolypeptide of approximately 25–30 <small>L</small>-lysine residues.<ref name="Shima">{{cite journal | author = Shima, S. and Sakai H. | year = 1977 | title = Polylysine produced by Streptomyces | journal = Agricultural and Biological Chemistry | volume = 41 | issue = 9 | pages = 1807–1809 | doi=10.1271/bbb1961.41.1807| doi-access = free }}</ref> According to research, ε-polylysine is adsorbed electrostatically to the cell surface of the bacteria, followed by a stripping of the [[Bacterial outer membrane|outer membrane]]. This eventually leads to the abnormal distribution of the [[cytoplasm]] causing damage to the bacterial cell<ref>{{cite journal | author = Shima, S.| year = 1984 | title = Antimicrobial action of ε-poly-L-lysine | journal = Journal of Antibiotics | volume = 37 | pages = 1449–1455 | pmid = 6392269 | issue = 11 | doi=10.7164/antibiotics.37.1449|display-authors=etal| doi-access = free }}</ref> that is produced by bacterial fermentation. ε-Poly-<small>L</small>-lysine is used as a natural preservative in food products.

{|class=wikitable

|+List of polylysines

!! !! L !! D !! Mixed

|-

! α

| poly-<small>L</small>-lysine (PLL) — coating

| poly-<small>D</small>-lysine (PDL) — coating

| synthesized, no applications

|-

! ε

| ε-polylysine, EPL — natural antibacterial

| colspan=2 | unheard of

|-

! Mixed

| dendric/branched polylysine — studied for RNA delivery<ref>{{cite journal | pmid=17373579 | year=2007 | last1=Eom | first1=K. D. | last2=Park | first2=S. M. | last3=Tran | first3=H. D. | last4=Kim | first4=M. S. | last5=Yu | first5=R. N. | last6=Yoo | first6=H. | title=Dendritic alpha,epsilon-poly(L-lysine)s as delivery agents for antisense oligonucleotides | journal=Pharmaceutical Research | volume=24 | issue=8 | pages=1581–1589 | doi=10.1007/s11095-006-9231-y | s2cid=43190567 }}</ref>

| colspan=2 | unheard of

|}

==Production==

Production of polylysine by natural fermentation is only observed in strains of bacteria in the genus ''[[Streptomyces]]''. ''[[Streptomyces albulus]]'' is most often used in scientific studies and is also used for the commercial production of ε-polylysine.

α-Polylysine is synthetically produced by a basic [[Condensation polymer|polycondensation]] reaction.<ref>{{Cite web | url=http://www.alamanda-polymers.com/content/poly-l-lysine-and-poly-d-lysine | title=Poly-L-Lysine and Poly-D-Lysine {{pipe}} Alamanda Polymers - Polyamino Acids, Superior by Design}}</ref>

==History==

{{missing information|section|other variants|date=October 2022}}

The production of ε-polylysine by natural fermentation was first described by researchers Shoji Shima and Heiichi Sakai in 1977.<ref name="Shima"/> Since the late 1980s, ε-polylysine has been approved by the Japanese [[Ministry of Health, Labour and Welfare]] as a preservative in food. In January 2004, ε-polylysine became [[generally recognized as safe]] (GRAS) certified in the United States.<ref name="FDA">[http://www.cfsan.fda.gov/~rdb/opa-g135.html GRAS Notice No. GRN 000135] {{webarchive|url=https://web.archive.org/web/20080511163336/http://www.cfsan.fda.gov/~rdb/opa-g135.html |date=2008-05-11 }}</ref>

== ε-Polylysine==

===In food===

ε-Polylysine is used commercially as a food [[preservative]] in Japan, Korea and in imported items sold in the United States. Food products containing polylysine are mainly found in Japan. The use of polylysine is common in food applications such as boiled rice, cooked vegetables, soups, [[noodles]] and sliced fish ([[sushi]]).<ref name="Hiraki">{{cite journal | doi = 10.1016/S0273-2300(03)00029-1 | author = Hiraki, J.| year = 2003 | title = Use of ADME studies to confirm the safety of ε-polylysine as a preservative in food | journal = [[Regulatory Toxicology and Pharmacology]] | volume = 37 | pages = 328–340 | pmid = 12726761 | issue = 2|display-authors=etal}}</ref>

Literature studies have reported an [[antimicrobial]] effect of ε-polylysine against [[yeast]], [[fungi]], [[Gram-positive bacteria]] and [[Gram-negative bacteria]].<ref>{{cite journal | author = Hiraki, J. | year = 1995 | title = Basic and applied studies on ε-polylysine | journal = Journal of Antibacterial Antifungal Agents | volume = 23 | pages = 349–354}}</ref>

Polylysine has a light yellow appearance and is slightly bitter in taste whether in powder or liquid form.

== α-Polylysine==

===In tissue culture===

α-Polylysine is commonly used to coat tissue cultureware as an attachment factor which improves cell adherence. This phenomenon is based on the interaction between the positively charged polymer and negatively charged cells or proteins. While the poly-<small>L</small>-lysine (PLL) precursor amino acid occurs naturally, the poly-<small>D</small>-lysine (PDL) precursor is an artificial product. The latter is therefore thought to be resistant to enzymatic degradation and so may prolong cell adherence.<ref>{{cite journal | doi = 10.1083/jcb.66.1.198 | author = Mazia, D.| year = 1975 | title = Adhesion of cells to surfaces coated with polylysine. Applications to electron microscopy. | journal = The Journal of Cell Biology | volume = 66 | pages = 198–200 | pmid = 1095595 | issue = 1|display-authors=etal | pmc=2109515}}</ref>

== Polylysine in drug delivery ==

Polylysine exhibits high positive charge density which allows it to form soluble complexes with negatively charged [[macromolecule]]s.<ref>{{Cite journal|last1=Park|first1=Tae Gwan|last2=Jeong|first2=Ji Hoon|last3=Kim|first3=Sung Wan|date=2006-07-07|title=Current status of polymeric gene delivery systems|journal=Advanced Drug Delivery Reviews|volume=58|issue=4|pages=467–486|doi=10.1016/j.addr.2006.03.007|issn=0169-409X|pmid=16781003}}</ref> Polylysine homopolymers or block copolymers have been widely used for delivery of DNA<ref>{{Cite journal|last1=Kadlecova|first1=Zuzana|last2=Rajendra|first2=Yashas|last3=Matasci|first3=Mattia|last4=Baldi|first4=Lucia|last5=Hacker|first5=David L.|last6=Wurm|first6=Florian M.|last7=Klok|first7=Harm-Anton|date=2013-08-10|title=DNA delivery with hyperbranched polylysine: a comparative study with linear and dendritic polylysine|journal=Journal of Controlled Release|volume=169|issue=3|pages=276–288|doi=10.1016/j.jconrel.2013.01.019|issn=1873-4995|pmid=23379996}}</ref> and proteins.<ref>{{Cite journal|last1=Jiang|first1=Yuhang|last2=Arounleut|first2=Phonepasong|last3=Rheiner|first3=Steven|last4=Bae|first4=Younsoo|last5=Kabanov|first5=Alexander V.|last6=Milligan|first6=Carol|last7=Manickam|first7=Devika S.|date=2016-06-10|title=SOD1 nanozyme with reduced toxicity and MPS accumulation|journal=Journal of Controlled Release|volume=231|pages=38–49|doi=10.1016/j.jconrel.2016.02.038|issn=1873-4995|pmid=26928528}}</ref> Polylysine-based [[nanoparticle]]s have also been shown to passively accumulate in the injured sites of [[Blood vessel|blood vessels]] after [[stroke]] due to incorporation into newly formed [[thrombus]],<ref>{{Cite journal|last1=Jiang|first1=Yuhang|last2=Brynskikh|first2=Anna M.|last3=S-Manickam|first3=Devika|last4=Kabanov|first4=Alexander V.|date=2015-09-10|title=SOD1 nanozyme salvages ischemic brain by locally protecting cerebral vasculature|journal=Journal of Controlled Release|volume=213|pages=36–44|doi=10.1016/j.jconrel.2015.06.021|issn=1873-4995|pmc=4684498|pmid=26093094}}</ref> which offers a new way to deliver therapeutic agents specifically to the sites of injury after vascular damage.

==Chemical modification==

In 2010, hydrophobically modified ε-polylysine was synthesized by reacting EPL with octenyl succinic anhydride (OSA).<ref>Yu, et al, J. Agri Food Chem, 2010 Jan 27;58(2):1290-5.</ref> It was found that OSA-g-EPLs had glass transition temperatures lower than EPL. They were able to form polymer [[micelles]] in water and to lower the surface tension of water, confirming their amphiphilic properties. The antimicrobial activities of OSA-g-EPLs were also examined, and the minimum inhibitory concentrations of OSA-g-EPLs against ''Escherichia coli'' O157:H7 remained the same as that of EPL. Therefore, modified EPLs have the potential of becoming bifunctional molecules, which can be used either as surfactants or emulsifiers in the encapsulation of water-insoluble drugs or as antimicrobial agents.

==References==

{{reflist}}

[[Category:Food additives]]

[[Category:Food preservatives]]

[[Category:Polymers]]

[[Category:Amino acid derivatives]]