16227-22-8

Upstream product

• 6913-23-1 2-thioxo-thiazolidin-5-one 
• 15028-44-1 DL-phenylalanine methyl ester 
• 56-40-6 glycine 
• 6206-42-4 N-benzyloxycarbonylglycyl-L-phenylalanine methyl ester 
• 106624-70-8 methyl (2S)-2-[[2-(t-butoxycarbonylamino)acetyl]amino]-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 811-98-3 d⁽⁴⁾-methanol 
• 129397-81-5 methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalaninate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 114479-32-2 (S)-2-(2-Isobutoxycarbonylamino-acetylamino)-3-phenyl-propionic acid methyl ester 
• 114479-31-1 Boc-D-Met-Gly-Phe-OMe 
• 114479-31-1 Boc-L-Met-Gly-Phe-OMe 
• 87242-56-6 Ac-ΔTyr(Ac)-(R)-Ala-Gly-(S)-Phe-OMe 
• 142929-43-9 N--3-<(triphenylmethyl)thio>-D-valyl>glycyl>-L-phenylalanine methyl ester 
• 500213-48-9 2-{2-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-acetylamino}-3-phenyl-propionic acid methyl ester 
• 808771-75-7 (S)-2-{2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-3-phenyl-propionic acid methyl ester 
• 66345-34-4 (S)-2-[2-((S)-2-Amino-3-methyl-butyrylamino)-acetylamino]-3-phenyl-propionic acid methyl ester 
• 863781-59-3 (S)-2-(2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-3-methyl-butyrylamino}-acetylamino)-3-phenyl-propionic acid methyl ester 
• 681253-71-4 2-{2-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-acetylamino}-3-phenyl-propionic acid 
• 681254-20-6 (2S,3R)-2-Benzyloxycarbonylamino-3-((S)-2-{2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-3-phenyl-propionyloxy)-butyric acid methyl ester 
• 681254-28-4 (2S,3R)-2-Benzyloxycarbonylamino-3-((S)-2-{2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-acetylamino}-3-phenyl-propionyloxy)-butyric acid methyl ester 
• 681254-36-4 (2S,3R)-2-Benzyloxycarbonylamino-3-((S)-2-{2-[(S)-2-{[(S)-1-((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-3-phenyl-propionyloxy)-butyric acid methyl ester 
• 87242-58-8 (S)-2-(2-{(R)-2-[(R)-3-(4-Acetoxy-phenyl)-2-acetylamino-propionylamino]-propionylamino}-acetylamino)-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of chiral 2,4-dichloro-6-menthoxy-1,3,5-triazines and 2- chloro-4,6-dimenthoxy-1,3,5-triazines as enantiodifferentiating coupling reagents. An x-ray study on 2,4,6-trimenthoxy-1,3,5-triazine

Chiral mono- di- and trimenthoxy-1,3,5-triazines ware obtained from natural menthol and cyanuric chloride and applied as enantioselective coupling reagents in the synthesis of dipeptides.

Synthesis and Characterization of a Series of Orthogonally Protected l-Carnosine Derivatives

l-Carnosine (β-alanyl-l-histidine) is an endogenous dipeptide that has been recognized for its broad spectrum of beneficial biological activities. However, the therapeutic utility of molecule has been hampered by its instability in human plasma (half-life

Instability of Amide Bond Comprising the 2-Aminotropone Moiety: Cleavable under Mild Acidic Conditions

An unusual hydrolysis/solvolysis of the classical acyclic amide bond, derived from N-troponylaminoethylglycine (Traeg) and α-amino acids, is described under mild acidic conditions. The reactivity of this amide bond is possibly owed to the protonation of the troponyl carbonyl functional group. The results suggest that the Traeg amino acid is a potential candidate for protecting and caging of the amine functional group of bioactive molecules via a cleavable amide bond.

"Backdoor Induction" of chirality in asymmetric hydrogenation with rhodium(I) complexes of amino acid substituted triphenylphosphane ligands

This paper describes the synthesis and characterization of 5-(diphenylphosphanyl)isophthalic acid bioconjugates (Lig-[R]2). In addition to symmetrically disubstituted conjugates with amino acids, peptides or amines, a convenient one-pot, two-step procedure for the synthesis of conjugates bearing two different substituents is reported. The 28 prepared phosphanes were used as monodentate ligands in the rhodium(I)-catalyzed hydrogenation of 2-acetamidoacrylate and (Z)-α-acetamidocinnamate. The ligand with the smallest side-chain substituents Lig-[Ala-OMe]2 (1a) revealed the highest selectivity, with up to 84 % ee. The catalysts presented herein are models of artificial metalloenzymes in which the outer-coordination sphere controls the selectivity in catalysis. The chirality of distant hydrogen-bonded amino acids is transmitted by "backdoor induction" to the prochiral RhI center. Models of artificial metalloenzymes are presented in which the outer-coordination sphere controls the selectivity in catalysis. The chirality of distant hydrogen-bonded amino acids or amines is transmitted by "backdoor induction" to the prochiral RhI center. Copyright

Synthesis and biological evaluation of Naloxone and Naltrexone-derived hybrid opioids

The synthesis and biological evaluation of hybrid opioids consisting of Naloxone or Naltrexone and a partial opioid peptide are described. These compounds were synthesized in a homogeneous solution as well as in solid phase. A hydrazone linkage was employed to connect the alkaloids to the tetrapeptides. In synthesizing the peptides some nontraditional methods, which provided excellent results, were explored. The solid phase synthesis was achieved by anchoring the Fmoc-Phe to the 2-chlorotrityl resin, followed by stepwise addition of two Fmoc-Gly units. Each addition step preceded by standard piperidine removal of the Fmoc from the prior amino acid (AA) residue. The final AA, Tyr, was added as its Boc derivative. The Boc-tetrapeptide was then separated from the resin with a TFE/AcOH/CH2Cl2 mixture. In the solution synthesis, each peptide elongation step was accomplished by one-pot removal of the Fmoc from the prior AA residue and addition of the next Fmoc-AA. TBAF-thiol was used to cleanly remove the Fmoc, before adding the next Fmoc-AA in the presence of DIPEA and TBTU. All prepared hybrid ligands exhibited high affinities toward all three opioid receptors; moderate preferences for κ and μ receptors over δ receptor were observed. [ 35S]GTPγS binding assays indicated that these hybrid opioids are δ and μ antagonists but partial κ agonist.

Synthesis of Sansalvamide A derivatives and their cytotoxicity in the MSS colon cancer cell line HT-29

We report the synthesis of thirty-six Sansalvamide A derivatives, and their biological activity against colon cancer HT-29 cell line, a microsatellite stable (MSS) colon cancer cell-line. The thirty-six compounds can be divided into three subsets, where t

Synthesis and cytotoxicity of novel Sansalvamide A derivatives

(Chemical Equation Presented) Described are the syntheses of 14 derivatives of the natural product Sansalvamide A, where two are more active against HCT 116 colon cancer cell lines than the natural product. These derivatives were synthesized using a combi

A progressive synthetic strategy for class B synergimycins

Described are the syntheses of four macrocyclic peptides that are the core structure of class B synergimycins, and the synthesis of a final class B derivative. Our synthetic route to these synergimycin derivatives allows the incorporation of amino acid su

Novel antibiotics: Second generation macrocyclic peptides designed to trap Holliday junctions

Described are the syntheses of 15 macrocyclic peptides designed to trap Holliday junctions (HJs) in bacteria during site-specific and homologous recombination. This leads to inhibiting bacterial growth. These second generation macrocycles were based on th

Novel antibiotics: macrocyclic peptides designed to trap Holliday junctions.

[reaction: see text] Described are the syntheses of eight macrocyclic peptides designed to trap Holliday junctions in bacteria, thereby inhibiting bacterial growth. These macrocycles were designed from linear dimerized hexapeptides that bind to the C-2 sy