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G5755

Sigma-Aldrich

Gly-Gly-Gly-Gly-Gly

Synonym(s):

Glycyl-glycyl-glycyl-glycyl-glycine, Pentaglycine

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About This Item

Linear Formula:
NH2CH2CO(NHCH2CO)3NHCH2COOH
CAS Number:
7093-67-6
Molecular Weight:
303.27
Beilstein:
1716946
EC Number:
230-398-3
MDL number:
MFCD00083696
UNSPSC Code:
12352200
PubChem Substance ID:
24895226
NACRES:
NA.26

Assay

≥98% (TLC)

form

solid

color

white

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

NCC(=O)NCC(=O)NCC(=O)NCC(=O)NCC(O)=O

InChI

1S/C10H17N5O6/c11-1-6(16)12-2-7(17)13-3-8(18)14-4-9(19)15-5-10(20)21/h1-5,11H2,(H,12,16)(H,13,17)(H,14,18)(H,15,19)(H,20,21)

InChI key

MXHCPCSDRGLRER-UHFFFAOYSA-N

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Biochem/physiol Actions

Pentaglycine forms interpeptide bridges in peptidogylcan crosslinking and may be used as a tether for markers such as green fluorescent protein (GFP). Pentaglycine may be used as a model peptide in oligoglycine separation technology development.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Aurelia Delaune et al.
PloS one, 6(2), e17054-e17054 (2011-03-10)
The WalKR two-component system is essential for viability of Staphylococcus aureus, a major pathogen. We have shown that WalKR acts as the master controller of peptidoglycan metabolism, yet none of the identified regulon genes explain its requirement for cell viability.
Hiroshi Tomoda
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 132(1), 37-44 (2012-01-05)
Methicillin-resistant Staphylococcus aureus (MRSA) is known as a major nosocomial pathogen that has also developed resistance to many antibiotics. Moreover, MRSA resistance to a last-resort antibiotic, vancomycin, has been reported. Therefore, new anti-infectious agents to prevent and treat MRSA infection
Alexander V Grishin et al.
Antibiotics (Basel, Switzerland), 9(12) (2020-12-23)
Antibacterial lysins are enzymes that hydrolyze bacterial peptidoglycan, which results in the rapid death of bacterial cells due to osmotic lysis. Lysostaphin is one of the most potent and well-studied lysins active against important nosocomial pathogen Staphylococcus aureus. Similarly to
Steffen Wöll et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 136, 203-212 (2019-01-25)
Conventional chemotherapy is associated with therapy-limiting side effects, which might be alleviated by targeted chemotherapeutics such as immunoliposomes. The targeting ligands of immunoliposomes are commonly attached by unspecific chemical conjugation, bearing risk of structural heterogeneity and therewith related biological consequences.
Christof Renner et al.
Molecular cancer, 9, 2-2 (2010-01-08)
It was previously demonstrated that the dipeptide carnosine inhibits growth of cultured cells isolated from patients with malignant glioma. In the present work we investigated whether carnosine also affects tumor growth in vivo and may therefore be considered for human
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