5060-32-2

Basic information

• Product Name: [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[3-[2-(2-hexanoylsulfanylethylcarbamoyl)ethylcarbamoyl]-3-hydroxy-2,2-dimethyl-propoxy]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosphonic acid
• Synonyms: [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[3-[2-(2-hexanoylsulfanylethylcarbamoyl)ethylcarbamoyl]-3-hydroxy-2,2-dimethyl-propoxy]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosphonic acid;Hexanoyl-CoA;hexanoyl-coenzyme A;Adenosine 3'-phosphoric acid 5'-[diphosphoric acid P2-[(R)-3-hydroxy-2,2-dimethyl-3-[[2-[[2-(hexanoylthio)ethyl]carbamoyl]ethyl]carbamoyl]propyl]] ester;C6:0-CoA;S-Hexanoylcoenzyme A
• CAS NO: 5060-32-2
• Molecular Formula: C₂₇H₄₆N₇O₁₇P₃S
• Molecular Weight: 865.68
• Mol File: 5060-32-2.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Density: 1.76 g/cm³
• Refractive Index: 1.685
• PKA: 1.16±0.50(Predicted)
• CAS DataBase Reference: [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[3-[2-(2-hexanoylsulfanylethylcarbamoyl)ethylcarbamoyl]-3-hydroxy-2,2-dimethyl-propoxy]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[3-[2-(2-hexanoylsulfanylethylcarbamoyl)ethylcarbamoyl]-3-hydroxy-2,2-dimethyl-propoxy]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosphonic acid(5060-32-2)
• EPA Substance Registry System: [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[3-[2-(2-hexanoylsulfanylethylcarbamoyl)ethylcarbamoyl]-3-hydroxy-2,2-dimethyl-propoxy]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosphonic acid(5060-32-2)

Safety Data

• Hazardous Substances Data: 5060-32-2(Hazardous Substances Data)

Usage

Definition

ChEBI: A medium-chain fatty acyl-CoA having hexanoyl as the S-acyl group.

InChI:InChI=1/C27H46N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h14-16,20-22,26,37-38H,4-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/t16-,20-,21-,22+,26-/m1/s1

Upstream product

• 142-62-1 hexanoic acid 
• 85-61-0 coenzyme A 
• 72531-43-2 C₉H₁₆O₄ 
• 1191-04-4 2-hexenoic acid 
• 6701-39-9 (2E)-hexenoyl-coenzyme A 
• 13419-69-7 (E)-2-Hexenoic acid 
• 132129-32-9 [5']adenylic acid hexanoic acid-anhydride 
• 288-32-4 1H-imidazole 
• 60988-34-3 1-(1-imidazolyl)-1-hexanone 

Downstream Products

• 81017-02-9 4-hydroxy-6-pentyl-2H-pyrone 
• 327175-05-3 4-hydroxy-6-(2-oxoheptyl)-2-pyrone 
• 111-27-3 hexan-1-ol 
• 1159918-23-6 6-(2-(2,4-dihydroxy-6-methylphenyl)-2-oxoethyl)-4-hydroxy-2-pyrone 
• 5665-89-4 1-(2,4,6-trihydroxyphenyl)hexan-1-one 
• 142-62-1 hexanoic acid 
• 6701-39-9 (2E)-hexenoyl-coenzyme A 
• 1184818-23-2 N-[2-(4-hydroxyphenyl)ethyl]hexanamide 
• 626-82-4 butyl hexanoate 
• 123-66-0 Ethyl hexanoate 
• 106-70-7 methyl hexanoate 
• 581800-17-1 AD₂₈₄a 

Relevant articles and documents

Identification of an α-Oxoamine Synthase and a One-Pot Two-Step Enzymatic Synthesis of α-Amino Ketones

Alb29, an α-oxoamine synthase involved in albogrisin biosynthesis in Streptomyces albogriseolus MGR072, was characterized and responsible for the incorporation of l-glutamate to acyl-coenzyme A substrates. Combined with Alb29 and Mgr36 (an acyl-coenzyme A ligase), a one-pot enzymatic system was established to synthesize seven α-amino ketones. When these α-amino ketones were fed into the alb29 knockout strain Δalb29, respectively, the albogrisin analogs with different side chains were observed.

In vitro studies of maleidride-forming enzymes

In vitro assays of enzymes involved in the biosynthesis of maleidrides from polyketides in fungi were performed. The results show that the enzymes are closely related to primary metabolism enzymes of the citric acid cycle in terms of stereochemical preferences, but with an expanded substrate selectivity. A key citrate synthase can react both saturated and unsaturated acyl CoA substrates to give solely anti substituted citrates. This undergoes anti-dehydration to afford an unsaturated precursor which is cyclised in vitro by ketosteroid-isomerase-like enzymes to give byssochlamic acid. This journal is

Screening and Engineering the Synthetic Potential of Carboxylating Reductases from Central Metabolism and Polyketide Biosynthesis

Carboxylating enoyl-thioester reductases (ECRs) are a recently discovered class of enzymes. They catalyze the highly efficient addition of CO2 to the double bond of α,β-unsaturated CoA-thioesters and serve two biological functions. In primary metabolism of many bacteria they produce ethylmalonyl-CoA during assimilation of the central metabolite acetyl-CoA. In secondary metabolism they provide distinct α-carboxyl-acyl-thioesters to vary the backbone of numerous polyketide natural products. Different ECRs were systematically assessed with a diverse library of potential substrates. We identified three active site residues that distinguish ECRs restricted to C4 and C5-enoyl-CoAs from highly promiscuous ECRs and successfully engineered a selected ECR as proof-of-principle. This study defines the molecular basis of ECR reactivity, allowing for predicting and manipulating a key reaction in natural product diversification.