Total Synthesis of (+)‐Blasticidin S

Ichikawa, Yoshiyasu; Hirata, Keiko; Ohbayashi, Masayoshi; Isobe, Mitsuaki

doi:10.1002/chem.200305358

Cited by 36 publications

(15 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…issue remodeling, such as that which occurs in embryonic development (1), adult wound healing (2,3), and female reproductive physiology (4,5), is accompanied by the growth of capillary blood vessels (angiogenesis) as well as capillary lymphatic vessels (lymphangiogenesis). This coupling of angiogenesis and lymphangiogenesis illustrates an important function of the lymphatic vasculature, which is to maintain fluid homeostasis by collecting fluid that leaks from capillary blood vessels and returning it to the blood circulation (6).…”

mentioning

confidence: 99%

Dose-dependent response of FGF-2 for lymphangiogenesis

Chang

García‐Cardeña²,

Farnebo³

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

256

195

View full text Add to dashboard Cite

Spatio-temporal studies on the growth of capillary blood vessels and capillary lymphatic vessels in tissue remodeling have suggested that lymphangiogenesis is angiogenesis-dependent. We revisited this concept by using fibroblast growth factor 2 (FGF-2) (80 ng) to stimulate the growth of both vessel types in the mouse cornea. When we lowered the dose of FGF-2 in the cornea 6.4-fold (12.5 ng), the primary response was lymphangiogenic. Further investigation revealed that vascular endothelial growth factor-C and -D are required for this apparent lymphangiogenic property of FGF-2, and when the small amount of accompanying angiogenesis was completely suppressed, lymphangiogenesis remained unaffected. Our findings demonstrate that there is a dose-dependent response of FGF-2 for lymphangiogenesis, and lymphangiogenesis can occur in the absence of a preexisting or developing vascular bed, i.e., in the absence of angiogenesis, in the mouse cornea.

show abstract

mentioning

confidence: 99%

Dose-dependent response of FGF-2 for lymphangiogenesis

Chang

García‐Cardeña²,

Farnebo³

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

256

195

View full text Add to dashboard Cite

show abstract

“…[11] Displacement of bromide 23 with sodium azide under phase-transfer conditions (NaN 3 , Bu 4 N·HSO 4 , CH 2 Cl 2 /aq. Acetylation of 20 followed by bromination was carried out in a simple one-pot process to afford a-bromo-tetra-O-acetylgalactopyranose 23.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Urea‐Tethered Disaccharides in Water

Ichikawa

Matsukawa

Tamura

et al. 2006

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

A new method for the synthesis of urea-linked disaccharides in aqueous media has been developed. The key feature of our approach is two strained Steyermark-type gluco- and galactopyranosyl oxazolidinones. Each oxazolidinone is attached to a pyranose ring in a di-equatorial trans-annulation framework. Reaction of these oxazolidinones with 4-aminohexopyranose in water proceeded smoothly to afford the urea-tethered cellobiose and lactose analogues. The galactose-type oxazolidinone proved to be more reactive than the glucose-type, which is explained by the presence of an axial hydroxy group at C4 in the former.

show abstract

“…Other important blasticidin-related nucleoside antibiotics that contain a β-amino moiety include cytomycin (681), cytosinine (682), gougerotin analogs (683), and bagougeramine (684) (Figure 32). 166 The syntheses of such derivatives start from readily available optically pure carbohydrates. Protected amino alcohol 686 containing a pyran skeleton [derived from 2-acetoxy-tri-Oacetyl-D-glucal (685) in seven steps] was subjected to hydroxymethyl oxidation and esterification to furnish β-amino ester 687.…”

Section: −165mentioning

confidence: 99%

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

View full text Add to dashboard Cite

Introduction 1116 2. Carbocyclic β-Amino Acids 1118 2.1. Syntheses of Five-or Six-Membered Carbocyclic β-Amino Acids 1118 2.1.1. Carbocyclic β-Amino Acids from β-Keto Esters 1119 2.1.2. Carbocyclic β-Amino Acids by Metathesis 1119 2.1.3. Carbocyclic β-Amino Acids by Amino Group Conjugate Addition 1122 2.1.4. Carbocyclic β-Amino Acids by Cycloaddition 1124 2.1.5. Carbocyclic β-Amino Acids by Desymmetrization of meso-Anhydrides 1124 2.1.6. Carbocyclic β-Amino Acids from Natural Sources 1125 2.1.7. Miscellaneous 1127 2.2. Syntheses of Small-Ring Carbocyclic β-Amino Acids 1128 2.3. Syntheses of Carbocyclic β-Amino Acids with Larger Ring Systems 1129 2.4. Synthesis of Functionalized Carbocyclic β-Amino Acids 1131 2.4.1. Syntheses of Functionalized Cyclic β-Amino Acids by C−C Double Bond Functionalization 1131 2.4.2. Several Relevant Routes to Functionalized Cyclic β-Amino Acids Other Than Functionalization of the Ring C−C Double Bond 1137 3. Cyclic β-Amino Acids with a Heteroatom in the Ring 1137 3.1. Syntheses of Cyclic β-Amino Acids with a N Atom in the Ring 1138 3.1.1. Three-and Four-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.2. Five-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.3. Six-Membered N-Containing Cyclic β-Amino Acids 1145 3.1.4. N-Containing Cyclic β-Amino Acids with Larger Ring Systems 1148 3.2. Syntheses of Cyclic β-Amino Acids with an O Atom in the Ring 1148 3.2.1. Four-Membered O-Containing Cyclic β-Amino Acids 1148 3.2.2. Five-Membered O-Containing Cyclic β-Amino Acids 1149 3.2.3. Six-Membered O-Containing Cyclic β-Amino Acids 1155 3.3. Cyclic β-Amino Acids with Other Heteroatoms in the Ring 1159 4. Some Relevant Biological Properties of Cyclic β-Amino Acids 1160 4.1. Cyclic β-Amino Acids Possessing Antifungal or Antibacterial Properties 1160 4.2. Antiviral Cyclic β-Amino Acids 1162 4.3. Cyclic β-Amino Acids with Antitumoral Properties 1162 4.4. Cyclic β-Amino Acids with Cardioprotective

show abstract

Total Synthesis of (+)‐Blasticidin S

Cited by 36 publications

References 61 publications

Dose-dependent response of FGF-2 for lymphangiogenesis

Dose-dependent response of FGF-2 for lymphangiogenesis

Synthesis of Urea‐Tethered Disaccharides in Water

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

Contact Info

Product

Resources

About