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[ CAS No. 142-73-4 ] {[proInfo.proName]}

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Chemical Structure| 142-73-4
Chemical Structure| 142-73-4
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Product Citations

Product Citations

Shegufta Farazi ; Martina H. Stenzel ; Robert Chapman DOI:

Abstract: Folding polymers into well-defined structures in solution is a critical step towards fully synthetic protein mimics. Peptide motifs such as diphenylalanine (FF) provide a versatile and thermally reversible way to guide the collapse of polymer chains in water, but there have been relatively few studies exploring their use to direct the folding of ‘single chain polymer nanoparticles’ (SCNPs) to date. Using a recently developed automated synthesis of multiblock peptide–DMA copolymers, we probe the effect that the peptide position and density as well as the overall size of the polymer has on SCNP folding, as measured by GPC and DOSY-NMR. We show that by controlling the position of the peptide within the polymer it is possible to form well-defined SCNPs, with levels of compaction close to globular proteins at relatively low levels of the folding motif. The tunability offered by both the sequence of the peptide and its position within the polymer makes these an excellent class of folding motifs for preparing water soluble and biocompatible SCNPs. Controlling the location of a folding motif within the backbone of a polymer chain can dramatically improve the folding of the polymer into single chain polymer nanoparticles (SCNPs).

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Product Details of [ 142-73-4 ]

CAS No. :142-73-4 MDL No. :MFCD00004280
Formula : C4H7NO4 Boiling Point : -
Linear Structure Formula :NH(CH2C(O)OH)2 InChI Key :NBZBKCUXIYYUSX-UHFFFAOYSA-N
M.W : 133.10 Pubchem ID :8897
Synonyms :
Iminodiacetic acid
Chemical Name :2,2'-Azanediyldiacetic acid

Calculated chemistry of [ 142-73-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 27.69
TPSA : 86.63 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.26
Log Po/w (XLOGP3) : -3.29
Log Po/w (WLOGP) : -1.25
Log Po/w (MLOGP) : -3.59
Log Po/w (SILICOS-IT) : -1.25
Consensus Log Po/w : -1.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : 1.67
Solubility : 6250.0 mg/ml ; 46.9 mol/l
Class : Highly soluble
Log S (Ali) : 2.04
Solubility : 14700.0 mg/ml ; 111.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.55
Solubility : 467.0 mg/ml ; 3.51 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 142-73-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 142-73-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 142-73-4 ]

[ 142-73-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 142-73-4 ]
  • [ 39987-25-2 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; at -10 - 20℃; Thionyl chloride (16 ml, 225.39 mmol, 1.64 g/ml) the addition was completed, iminodiacetic acid3(10 g, 75.13 mmol) was added and the reaction was transferred to room temperature,stiringovernight. Methanol was removed under vacuum to give the compound4(14.70 g, 99 %) as a white solid.1H NMR (400 MHz, DMSO) delta10.05 (s, 2H), 4.01 (s, 4H), 3.74 (s, 6H). HRMS (ESI) (m/z):calcdfor C6H11NO4[M+H]+ 162.0755, found. 162.0766.
99% With thionyl chloride; at -10 - 20℃; At -10 , pressure-equalizing dropping funnel was added thionyl chloride (16ml, 225.39mmol, 1.64g / ml)To 100 ml of methanol, add imine diacetate (10 g, 75.13 mmol),The reaction solution was transferred to room temperature and stirred overnight. The reaction solution was swirled to remove methanol to obtain Compound 3 (14.70 g, 99%) as a white solid.
81% Methanol (500 mL) was cooled to -20 C, and SOCl2 (36 mL, 0.5 mol) was added dropwise under vigorous stirring while maintaining the temperature of the reaction mixture below -10 C. Iminodiacetic acid(13.3 g, 0.1 mol) was then added in one portion. The reaction mixture was stirred for 24 h at r.t. and then left to stand at r.t. for two days.The volatiles were evaporated, and the residue were crystallized from methanol. Yield: 16 g (81%); white crystalline solid.1H NMR (300 MHz, D2O): delta = 4.13 (s, 4 H), 3.85 (s, 6 H).13C NMR (75 MHz, D2O): delta = 168.08, 54.12, 47.66. Anal. Calcd for C6H12ClNO4: C, 36.47; H, 6.12; N, 7.09. Found: C, 36.52;H, 6.01; N, 6.98.
  • 2
  • CO3(2-)*Cu2(OH)2(2+) [ No CAS ]
  • [ 272-97-9 ]
  • [ 142-73-4 ]
  • [copper(II)(iminodiacetate)(5-azabenziimidazole)]*2H2O [ No CAS ]
  • 3
  • [ 3153-26-2 ]
  • [ 17217-57-1 ]
  • [ 7732-18-5 ]
  • [ 142-73-4 ]
  • [VO(IDA)(4,4'-dimethoxy-2,2'-dipyridyl)]*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 70℃; for 0.416667h; General procedure: The solutions contained 1) VO(acac)2 (5.3 g, 20.0 mmol), H2IDA (2.66 g, 20.0 mmol) and dmbipy (3.68 g, 17.0 mmol) in water (100 mL) and 2) VO(acac)2 (5.3 g, 20.0 mmol), mH2IDA (2.94 g,20.0 mmol) and dmbipy (3.68 g, 17.0 mmol) in water (100 mL) were heated about 25 min at 70°C in a heating mantle. Then, after several days, dark green crystals of [VO(mIDA)(dmbipy)*]1.5H2O and the grey-green powder of [VO(IDA)(dmbipy)]*2H2O were obtained. The composition of the studied compounds was established on the basis of the elemental analysis of carbon, hydrogen and nitrogen (CARBO ERBA type CHNS e O 1108). Anal. Calcd for [VO(mIDA)(dmbipy)]*1.5H2O (percent): C, 42.20, H, 4.84, N, 9.23. Found:C, 42.54, H, 4.94, N, 9.03. Anal. Calcd for [VO(IDA)(dmbipy)]*2H2O(percent): C, 42.67, H, 4.67, N, 9.33. Found: C, 42.43, H, 4.78, N, 9.17.
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