Boc-11-aminoundecanoic acid

 CAS No.: 10436-25-6  Cat No.: BP-500451  Purity: ≥ 95% 4.5  

Boc-11-aminoundecanoic acid is a protected, long-chain amino acid building block featuring an N-Boc (tert-butoxycarbonyl) group and an eleven-carbon aliphatic linker terminated by a carboxylic acid. Its extended, flexible hydrocarbon spacer provides a predictable distance and conformational freedom between functional handles, while the Boc group enables selective amide or coupling chemistry under standard peptide-linker conditions and can be removed when required to expose the primary amine for further conjugation. In PROTAC and targeted protein degradation workflows, such linkers are used to tune the spatial relationship between the ligand that recruits the E3 ligase and the ligand that binds the target protein, thereby optimizing ternary complex formation and degradation potency. The compound’s utility lies in its compatibility with common amide-bond-forming strategies, allowing researchers to construct modular, chemically stable conjugates for systematic structure–activity studies and linker-length optimization.

Boc-11-aminoundecanoic acid

Structure of 10436-25-6

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Category
PROTAC Linker
Molecular Formula
C16H31NO4
Molecular Weight
301.42
Appearance
White solid

* For research and manufacturing use only. Not for human or clinical use.

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Popular Publications Citing BOC Sciences Products
Purity
≥ 95%
Appearance
White solid
Storage
Store at 2-8 °C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
11-[(2-methylpropan-2-yl)oxycarbonylamino]undecanoic acid
Synonyms
Boc-NH-(CH2)10-COOH; 11-(Boc-amino)-undecanoic acid; 11-((tert-Butoxycarbonyl)amino)undecanoic acid; 11-[(tert-butoxycarbonyl)amino]undecanoic acid; 11-[(2-methylpropan-2-yl)oxycarbonylamino]undecanoic Acid; Boc-11-Aun-OH; Boc-Aund(11)-OH; N-BOC-11-aminoundecanoic acid; Boc 11 Aun OH
Boiling Point
441.9±18.0 °C (Predicted)
Melting Point
67-68 °C
Density
1.006±0.06 g/cm3 (Predicted)
InChI Key
HPTPZJBSQUULAV-UHFFFAOYSA-N
InChI
InChI=1S/C16H31NO4/c1-16(2,3)21-15(20)17-13-11-9-7-5-4-6-8-10-12-14(18)19/h4-13H2,1-3H3,(H,17,20)(H,18,19)
SMILES
CC(C)(C)OC(=O)NCCCCCCCCCCC(=O)O
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.

This Boc-protected amino acid linker is designed for modular assembly of PROTACs, providing a chemically stable handle that can be selectively unmasked and coupled under standard peptide-conjugation conditions. Its aliphatic spacer supports productive spatial presentation between binding elements, while the Boc group enables controlled functional-group management during synthesis. The following sections describe the structure and the practical reactivity considerations relevant to constructing targeted protein degraders.

Structure: Boc-11-aminoundecanoic acid is a long-chain amino acid featuring an N-Boc carbamate protecting group, a terminal carboxylic acid, and an extended aliphatic methylene-rich backbone. It contains amide-like carbamate bonding, a carboxylic acid functionality for activation, and conformational flexibility suitable for linker design.

Reactivity: The carboxylic acid can be converted to activated esters or coupling partners to form amide bonds with amine-bearing PROTAC fragments, typically using peptide coupling reagents under anhydrous conditions with base. The Boc group is removable under acid-mediated deprotection to reveal a primary amine for subsequent coupling. Reaction planning should account for protecting-group compatibility and minimizing racemization where stereochemical retention is required.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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