137173-46-7 Usage
Description
DDHL, also known as Dodecanoyl-L-homoserine lactone, is an N-acyl-L-homoserine lactone with dodecanoyl as the acyl substituent. It is an active quorum sensing modulator first recognized in Sinorhizobium meliloti. DDHL plays a crucial role in cell communication and regulation within and between bacterial species.
Uses
Used in Bacterial Communication:
DDHL is used as a quorum sensing modulator for regulating cell communication and regulation in various bacterial species. The length of the acyl chain in DDHL is the most significant variable defining its function, with shorter chains displaying opposing actions to the longer chains.
Used in Microbiology Research:
DDHL is used as a research tool for studying the mechanisms of bacterial communication, quorum sensing, and the development of new strategies to control bacterial populations and infections.
Used in Pharmaceutical Development:
DDHL is used as a potential target for the development of new antimicrobial agents that can disrupt bacterial communication and regulation, leading to the control of bacterial infections and the prevention of antibiotic resistance.
Biochem/physiol Actions
N-Dodecanoyl-L-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, cell to cell communication among bacteria; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.
Check Digit Verification of cas no
The CAS Registry Mumber 137173-46-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,7,1,7 and 3 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 137173-46:
(8*1)+(7*3)+(6*7)+(5*1)+(4*7)+(3*3)+(2*4)+(1*6)=127
127 % 10 = 7
So 137173-46-7 is a valid CAS Registry Number.
InChI:InChI=1/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1
137173-46-7Relevant articles and documents
Long-chain acyl-homoserine lactones from Methylobacterium mesophilicum: Synthesis and absolute configuration
Pomini, Armando M.,Cruz, Pedro L. R.,Gai, Claudia,Araujo, Welington L.,Marsaioli, Anita J.
supporting information; experimental part, p. 2125 - 2129 (2010/04/05)
The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.
