tetra-Boc-spermine-5-carboxylic acid
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tetra-Boc-spermine-5-carboxylic acid

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tetra-Boc-spermine-5-carboxylic acid is a spermidine derivative used in nucleic acid transfer reactions, and in the synthesis of degradable multivalent cationic lipids with disulfide-bond spacers for gene delivery.

Category
BOC-Amino Acids
Catalog number
BAT-007755
CAS number
119798-08-2
Molecular Formula
C31H58N4O10
Molecular Weight
646.82
tetra-Boc-spermine-5-carboxylic acid
IUPAC Name
(2S)-2,5-bis[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]pentanoic acid
Synonyms
Boc4-Sper-COOH; N-α,δ-Bis-Boc-N-a,d-bis(3-Boc-aminopropyl)-L-ornithine; (10S)​-2,​2,​21,​21-​tetramethyl-​4,​19-​dioxo-3,​20-​Dioxa-​5,​9,​14,​18-​tetraazadocosane-​9,​10,​14-​tricarboxylic acid 9,​14-​bis(1,​1-​dimethylethyl) ester; (S)-2,2,21,21-tetramethyl-4,19-dioxo-3,20-Dioxa-5,9,14,18-tetraazadocosane-9,10,14-tricarboxylic acid 9,14-bis(1,1-dimethylethyl) ester; Tetra-BOC-ACP; (2S)-2,5-bis[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]pentanoic acid; Tetra BOC ACP
Appearance
White powder
Purity
≥ 97% (HPLC)
Density
1.112±0.06 g/cm3 (Predicted)
Melting Point
67-70 °C
Boiling Point
737.1±60.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C31H58N4O10/c1-28(2,3)42-24(38)32-17-14-20-34(26(40)44-30(7,8)9)19-13-16-22(23(36)37)35(27(41)45-31(10,11)12)21-15-18-33-25(39)43-29(4,5)6/h22H,13-21H2,1-12H3,(H,32,38)(H,33,39)(H,36,37)/t22-/m0/s1
InChI Key
HSPKBBVFWXCYJN-QFIPXVFZSA-N
Canonical SMILES
CC(C)(C)OC(=O)NCCCN(CCCC(C(=O)O)N(CCCNC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
1. Acidity characterization of heterogeneous catalysts by solid-state NMR spectroscopy using probe molecules
Anmin Zheng, Shang-Bin Liu, Feng Deng Solid State Nucl Magn Reson. 2013 Oct-Nov;55-56:12-27. doi: 10.1016/j.ssnmr.2013.09.001. Epub 2013 Sep 20.
Characterization of the surface acidic properties of solid acid catalysts is a key issue in heterogeneous catalysis. Important acid features of solid acids, such as their type (Brønsted vs. Lewis acid), distribution and accessibility (internal vs. external sites), concentration (amount), and strength of acid sites are crucial factors dictating their reactivity and selectivity. This short review provides information on different solid-state NMR techniques used for acidity characterization of solid acid catalysts. In particular, different approaches using probe molecules containing a specific nucleus of interest, such as pyridine-d5, 2-(13)C-acetone, trimethylphosphine, and trimethylphosphine oxide, are compared. Incorporation of valuable information (such as the adsorption structure, deprotonation energy, and NMR parameters) from density functional theory (DFT) calculations can yield explicit correlations between the chemical shift of adsorbed probe molecules and the intrinsic acid strength of solid acids. Methods that combine experimental NMR data with DFT calculations can therefore provide both qualitative and quantitative information on acid sites.
2. The Stephan Curve revisited
William H Bowen Odontology. 2013 Jan;101(1):2-8. doi: 10.1007/s10266-012-0092-z. Epub 2012 Dec 6.
The Stephan Curve has played a dominant role in caries research over the past several decades. What is so remarkable about the Stephan Curve is the plethora of interactions it illustrates and yet acid production remains the dominant focus. Using sophisticated technology, it is possible to measure pH changes in plaque; however, these observations may carry a false sense of accuracy. Recent observations have shown that there may be multiple pH values within the plaque matrix, thus emphasizing the importance of the milieu within which acid is formed. Although acid production is indeed the immediate proximate cause of tooth dissolution, the influence of alkali production within plaque has received relative scant attention. Excessive reliance on Stephan Curve leads to describing foods as "safe" if they do not lower the pH below the so-called "critical pH" at which point it is postulated enamel dissolves. Acid production is just one of many biological processes that occur within plaque when exposed to sugar. Exploration of methods to enhance alkali production could produce rich research dividends.
3. Dietary Acid Load Associated with Hypertension and Diabetes in the Elderly
Tulay Omma, Nese Ersoz Gulcelik, Fatmanur Humeyra Zengin, Irfan Karahan, Cavit Culha Curr Aging Sci. 2022 Aug 4;15(3):242-251. doi: 10.2174/1874609815666220328123744.
Background: Diet can affect the body's acid-base balance due to its content of acid or base precursors. There is conflicting evidence for the role of metabolic acidosis in the development of cardiometabolic disorders, hypertension (HT), and insulin resistance (IR). Objective: We hypothesized that dietary acid load (DAL) is associated with adverse metabolic risk factors and aimed to investigate this in the elderly. Methods: A total of 114 elderly participants were included in the study. The participants were divided into four groups, such as HT, diabetes (DM), both HT and DM, and healthy controls. Anthropometric, biochemical, and clinical findings were recorded. Potential renal acid load (PRAL) and net endogenous acid production (NEAP) results were obtained for three days, 24-hour dietary records via a nutrient database program (BeBiS software program). Results: The groups were matched for age, gender, and BMI. There was a statistically significant difference between the groups regarding NEAP (p =0.01) and no significant difference for PRAL ( p = 0.086). The lowest NEAP and PRAL levels were seen in the control group while the highest in the HT group. Both NEAP and PRAL were correlated with waist circumference (r = 0,325, p = 0.001; r=0,231, p =0,016, respectively). Conclusion: Our data confirmed that subjects with HT and DM had diets with greater acid-forming potential. High NEAP may be a risk factor for chronic metabolic diseases, particularly HT. PRAL could not be shown as a significantly different marker in all participants. Dietary content has a significant contribution to the reduction of cardiovascular risk factors, such as HT, DM, and obesity.
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